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Hangzhou Think Chemical Co. Ltd

Solithromycin CAS No.:760981-83-7 Name: Solithromycin Synonyms: CEM 101; OP 1068 Molecular Structure: Molecular Formula: C43H65FN6O10 Molecular Weight: 845.01 CAS Reg

High purity Solithromycin CAS No.:760981-83-7

Cas:760981-83-7

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Henan Tianfu Chemical Co., Ltd.

Our company engages in Sodium Tripolyphosphate (STPP) and Sodium Hexametabphosphate (SHMP) production; development of noble metal catalysts, synthesis of electronic chemical materials and general chemicals Imp&Exp trading business. The company

TIANFU-CHEM - SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Pharmaceutical Grade CAS 760981-83-7 with competitive price

Cas:760981-83-7

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hangzhou Sartort Biopharma Co., Ltd

Appearance:White to off-white powder Storage:R.T Package:25kg/Barrel Application:A new type of ketolactone (ie macrolide) antibiotic Transportation:Express/Sea/Air Port:Any port in China

High quality raw materials Solithromycin

Cas:760981-83-7

Min.Order:50 Gram

FOB Price: $20.0 / 60.0

Type:Lab/Research institutions

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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

SOLITHROMYCIN 760981-83-7

Cas:760981-83-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Leader Biochemical Group

About Product Details Items Specifications Test Results Appearance White to white crystalline powde

China Biggest Factory Manufacturer Supply SOLITHROMYCIN CAS 760981-83-7

Cas:760981-83-7

Min.Order:100 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

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Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At prese

Solithromycin 99%

Cas:760981-83-7

Min.Order:1 Gram

FOB Price: $48.0 / 60.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, steroids, pharmaceutical

SOLITHROMYCIN/760981-83-7/High quality SOLITHROMYCIN

Cas:760981-83-7

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

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Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need C

SOLITHROMYCIN manufacturer with low price

Cas:760981-83-7

Min.Order:1 Gram

Negotiable

Type:Trading Company

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Hebei Quanhe Biotechnology Co. LTD

1. Timely and efficient service to ensure communication with customers 2. Produce products of different specifications and sizes according to your requirements. 3. Quality procedures and standards recognized by SGS. Advanced plant equipment ensures s

SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Kilogram

FOB Price: $50.0 / 100.0

Type:Lab/Research institutions

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

SOLITHROMYCIN

Cas:760981-83-7

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

OP-1068 CEM-101 Solithromycin 760981-83-7

Cas:760981-83-7

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

High quality SOLITHROMYCIN

Cas:760981-83-7

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

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Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

Solithromycin Manufacturer/High quality/Best price/In stock

Cas:760981-83-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

SOLITHROMYCINhotsalesinstock

Cas:760981-83-7

Min.Order:1 Milligram

Negotiable

Type:Trading Company

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EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

TIANFUCHEM--SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

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Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd.established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World. Hu

Solithromycin

Cas:760981-83-7

Min.Order:0

Negotiable

Type:Trading Company

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Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W

TIANFUCHEM--SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

TIANFUCHEM--SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

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Senova Technology Company Limited

We have most reliable quality, competitive prices and full documents for this APIs 1. GMP WORKSHOP 2. DMF Application:Antibacteria

Solithromycin

Cas:760981-83-7

Min.Order:100 Gram

Negotiable

Type:Trading Company

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Wuhu Nuowei Chemistry Technologies Co., Ltd.

Wuhu Nuovo Chemical Technology Co., Ltd. was established in August 2014, mainly engaged in the development, production and sales of ionic liquids, ribose, nucleosides, nucleotides and related chemicals; Products are mainly used in new energy, new ma

Solithromycin

Cas:760981-83-7

Min.Order:100 Gram

Negotiable

Type:Manufacturers

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Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

TIANFUCHEM--SOLITHROMYCIN

Cas:760981-83-7

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

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Hangzhou Dingyan Chem Co., Ltd

manufacture Application:The refence standard products, for lab use, also we could produce bigger quantity on yr requirement.

Solithromycin

Cas:760981-83-7

Min.Order:0

Negotiable

Type:Lab/Research institutions

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HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white crystalline powder Storage:Sealed in a cool ,dry and microtherm place , avoid light . Package:100g/bottle,1kg/bottle,25kg/drum or as per your request Application:It is an impo

760981-83-7 supplier in China

Cas:760981-83-7

Min.Order:100 Gram

Negotiable

Type:Trading Company

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BOC Sciences

BOC Sciences is committed to supplying cost-effective products and services. We provide Solithromycin. Solithromycin, also known as CEM-101 and OP-1068, is a ketolide antibiotic undergoing clinical development for the treatment of community-acquire

Solithromycin

Cas:760981-83-7

Min.Order:1 Gram

Negotiable

Type:Trading Company

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Hubei Taiho Chemical Co.,LTD

TAIHO Unique Advantages:1.We're factory2.Free samples available3.Commodity inspection can be done4.ISO9001,Kosher certifications5.10 years experiences Storage:Store in cool &dry place Package:aluminium foil bag/fiber can/plastic drum Application:comp

Solithromycin

Cas:760981-83-7

Min.Order:0

Negotiable

Type:Manufacturers

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Hangzhou J&H Chemical Co., Ltd.

J&H CHEM is one of China's leading providers of integrated fine chemical services including offering, research and development, Custom manufacturing business, as well as other Value-added customer services, for diversified range products of chemicals

SOLITHROMYCIN

Cas:760981-83-7

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Xian Changyue Biological Technology Co., Ltd.

best seller Application:API

SOLITHROMYCIN

Cas:760981-83-7

Min.Order:0

Negotiable

Type:Manufacturers

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Synthetic route

C50H69FN6O11

C50H69FN6O11

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 40℃; for 24h;98%
With methanol at 40℃;97.7%
With methanol at 20℃; for 16h;0.2 g
1-(4-aminobutyl)-4-(3-aminophenyl)-1H-1,2,3-triazole

1-(4-aminobutyl)-4-(3-aminophenyl)-1H-1,2,3-triazole

C36H54FN3O12

C36H54FN3O12

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
With Imidazole hydrochloride at 60℃;95%
Stage #1: C36H54FN3O12 at 23℃; under 0.1 Torr; for 12h;
Stage #2: 1-(4-aminobutyl)-4-(3-aminophenyl)-1H-1,2,3-triazole With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 45℃; for 2h;
79 mg
11-N-(4-azido-butyl)-6-O-methyl-5-desosamynyl-3-oxo-2-fluoro-erythronolide A 11,12-carbamate

11-N-(4-azido-butyl)-6-O-methyl-5-desosamynyl-3-oxo-2-fluoro-erythronolide A 11,12-carbamate

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol for 16h;69%
With copper(l) iodide In toluene at 70℃; for 16h;17 mg
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 24h;
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 24h; Reagent/catalyst; Huisgen Cycloaddition;
C48H82N2O18S

C48H82N2O18S

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere
2.1: hydrogenchloride / methanol; water / 20 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
3.2: 2 h / -78 - 20 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
4.2: 2 h / 0 - 20 °C / Inert atmosphere
5.1: methanol / 3 h / Inert atmosphere; Reflux
6.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
C47H79N5O15
849407-73-4

C47H79N5O15

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / methanol; water / 20 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
2.2: 2 h / -78 - 20 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 20 °C / Inert atmosphere
4.1: methanol / 3 h / Inert atmosphere; Reflux
5.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
acetic acid 2-[1-(4-azido-butyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
849407-74-5

acetic acid 2-[1-(4-azido-butyl)-4-ethyl-8-hydroxy-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 - 20 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
3.1: methanol / 3 h / Inert atmosphere; Reflux
4.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
11-N-(4-azido-butyl)-6-O-methyl-5-(2-acetyl-desosamynyl)-3-oxo-erythronolide A 11,12-carbamate
760981-81-5

11-N-(4-azido-butyl)-6-O-methyl-5-(2-acetyl-desosamynyl)-3-oxo-erythronolide A 11,12-carbamate

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: methanol / 3 h / Inert atmosphere; Reflux
3.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
clarithromycin
81103-11-9

clarithromycin

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 72 h / 35 °C / Inert atmosphere
3.1: N,N-dimethyl-formamide / 48 h / 35 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
5.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere
6.1: hydrogenchloride / methanol; water / 20 h / 20 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
7.2: 2 h / -78 - 20 °C / Inert atmosphere
8.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
8.2: 2 h / 0 - 20 °C / Inert atmosphere
9.1: methanol / 3 h / Inert atmosphere; Reflux
10.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: triethylamine / ethyl acetate / 24 h / 20 - 25 °C
2.1: hydrogenchloride / water; ethanol / 1.5 h
3.1: pyridine / dichloromethane / 1 h / -20 - 5 °C / Inert atmosphere
4.1: pyridinium chlorochromate / dichloromethane / 24 h / 20 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 24 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -25 - -20 °C / Inert atmosphere
6.2: 1 h / -15 - -10 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 55 - 65 °C
8.1: potassium tert-butylate / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere
8.2: 1.5 h / -25 - -20 °C
9.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C / Inert atmosphere
10.1: methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: triethylamine / ethyl acetate / 24 h / 20 - 25 °C
2.1: hydrogenchloride / water; ethanol / 1.5 h
3.1: pyridine / dichloromethane / 1 h / -20 - 5 °C / Inert atmosphere
4.1: pyridinium chlorochromate / dichloromethane / 24 h / 20 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 24 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -25 - -20 °C / Inert atmosphere
6.2: 1 h / -15 - -10 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 55 - 60 °C
8.1: pyridine / 2 h / 0 - 10 °C
9.1: sodium azide / N,N-dimethyl-formamide / 8 h / 20 °C
10.1: potassium tert-butylate / tetrahydrofuran / 1 h / -30 - -20 °C / Inert atmosphere
10.2: 1.5 h / -25 - -20 °C
11.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / acetonitrile / 20 °C / Inert atmosphere
12.1: methanol / 16 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: dmap; triethylamine / ethyl acetate / 16 h / 70 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24.5 h / 28 °C
3.1: hydrogenchloride / acetone; water / 12 h / 40 °C
4.1: dimethylsulfide / dichloromethane / 4 h / -20 °C
4.2: 1.5 h / -20 - 25 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; dimethyl sulfoxide / 24 h / 25 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -35 °C
6.2: 2 h / -35 - 25 °C
7.1: hydrogenchloride / water; methanol / 24 h / 40 °C
View Scheme
11-N-(4-azido-butyl)-6-O-methyl-5-(2-acetyl-desosamynyl)-3-oxo-2-fluoro-erythronolide A 11,12-carbamate

11-N-(4-azido-butyl)-6-O-methyl-5-(2-acetyl-desosamynyl)-3-oxo-2-fluoro-erythronolide A 11,12-carbamate

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 3 h / Inert atmosphere; Reflux
2: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
2',4''-di-O-acetyl-6-O-methylerythromycin A
152235-55-7

2',4''-di-O-acetyl-6-O-methylerythromycin A

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 72 h / 35 °C / Inert atmosphere
2.1: N,N-dimethyl-formamide / 48 h / 35 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
4.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere
5.1: hydrogenchloride / methanol; water / 20 h / 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
6.2: 2 h / -78 - 20 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
7.2: 2 h / 0 - 20 °C / Inert atmosphere
8.1: methanol / 3 h / Inert atmosphere; Reflux
9.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A
217977-00-9

10,11-anhydro-2',4''-di-O-acetyl-12-O-(imidazol-1-ylcarbonyl)-6-O-methylerythromycin A

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: N,N-dimethyl-formamide / 48 h / 35 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere
4.1: hydrogenchloride / methanol; water / 20 h / 20 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 - 20 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
6.2: 2 h / 0 - 20 °C / Inert atmosphere
7.1: methanol / 3 h / Inert atmosphere; Reflux
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
C47H80N2O16
849407-71-2

C47H80N2O16

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
2.1: sodium azide / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere
3.1: hydrogenchloride / methanol; water / 20 h / 20 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
4.2: 2 h / -78 - 20 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 2 h / 0 - 20 °C / Inert atmosphere
6.1: methanol / 3 h / Inert atmosphere; Reflux
7.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C
View Scheme
(R)-3-hydroxy-2-methylpent-1-ene
125637-07-2

(R)-3-hydroxy-2-methylpent-1-ene

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
2.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
3.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7.1: 130 °C
8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
8.2: 0.58 h / 23 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
10.1: 12 h / 23 °C / 0.1 Torr
10.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
2.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
3.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
8.2: 0.58 h / 23 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
10.1: 12 h / 23 °C / 0.1 Torr
10.2: 2 h / 45 °C
View Scheme
(R)-tert-butyldimethyl((2-methylpent-1-en-3-yl)oxy)silane
135393-98-5

(R)-tert-butyldimethyl((2-methylpent-1-en-3-yl)oxy)silane

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
2.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6.1: 130 °C
7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
7.2: 0.58 h / 23 °C
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
9.1: 12 h / 23 °C / 0.1 Torr
9.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 9 steps
1.1: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / water; tetrahydrofuran / 3 h
2.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
7.2: 0.58 h / 23 °C
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
9.1: 12 h / 23 °C / 0.1 Torr
9.2: 2 h / 45 °C
View Scheme
(R)-3-((tert-butyldimethylsilyl)oxy)pentan-2-one
220018-22-4

(R)-3-((tert-butyldimethylsilyl)oxy)pentan-2-one

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
6.2: 0.58 h / 23 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
8.1: 12 h / 23 °C / 0.1 Torr
8.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 8 steps
1.1: lithium chloride / tetrahydrofuran / 1.1 h / -20 °C
2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5.1: 130 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
6.2: 0.58 h / 23 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
8.1: 12 h / 23 °C / 0.1 Torr
8.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 8 steps
1: lithium (1S,2R)-1-phenyl-2-(pyrrolidin-1-yl)-1-propanolate
2: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
3: Dess-Martin periodane
4: tetrabutyl ammonium fluoride
5: chlorobenzene / 132 °C
6: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
7: 1,8-diazabicyclo[5.4.0]undec-7-ene
8: Imidazole hydrochloride / 60 °C
View Scheme
C37H61N5O12

C37H61N5O12

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol / 24 h / 23 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
2.2: 1 h / -78 °C
3.1: sodium L-ascorbate; copper(II) sulfate / water; tert-butyl alcohol / 16 h
View Scheme
11-N-(4-azido-butyl)-6-O-methyl-5-O-desosaminyl-3-oxo-erythronolide A 11,12-carbamate
849407-75-6

11-N-(4-azido-butyl)-6-O-methyl-5-O-desosaminyl-3-oxo-erythronolide A 11,12-carbamate

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
1.2: 1 h / -78 °C
2.1: sodium L-ascorbate; copper(II) sulfate / water; tert-butyl alcohol / 16 h
View Scheme
(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-2,4-dimethylpentanal

(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-2,4-dimethylpentanal

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
1.2: 12 h / -78 °C
2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
8.1: 130 °C
9.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
9.2: 0.58 h / 23 °C
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
11.1: 12 h / 23 °C / 0.1 Torr
11.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 11 steps
1.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
1.2: 12 h / -78 °C
2.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
3.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
5.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
6.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
8.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
9.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
9.2: 0.58 h / 23 °C
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
11.1: 12 h / 23 °C / 0.1 Torr
11.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 11 steps
1: zinc(II) chloride
2: silver trifluoromethanesulfonate
3: hydrogen fluoride / water
4: Dess-Martin periodane
5: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
6: Dess-Martin periodane
7: tetrabutyl ammonium fluoride
8: chlorobenzene / 132 °C
9: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
10: 1,8-diazabicyclo[5.4.0]undec-7-ene
11: Imidazole hydrochloride / 60 °C
View Scheme
C41H75NO12Si

C41H75NO12Si

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
3.1: 130 °C
4.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
4.2: 0.58 h / 23 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
6.1: 12 h / 23 °C / 0.1 Torr
6.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 6 steps
1.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
3.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
4.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
4.2: 0.58 h / 23 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
6.1: 12 h / 23 °C / 0.1 Torr
6.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 6 steps
1: Dess-Martin periodane
2: tetrabutyl ammonium fluoride
3: chlorobenzene / 132 °C
4: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
5: 1,8-diazabicyclo[5.4.0]undec-7-ene
6: Imidazole hydrochloride / 60 °C
View Scheme
C41H73NO12Si

C41H73NO12Si

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
2.1: 130 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
3.2: 0.58 h / 23 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
5.1: 12 h / 23 °C / 0.1 Torr
5.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 5 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
2.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
3.2: 0.58 h / 23 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
5.1: 12 h / 23 °C / 0.1 Torr
5.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 5 steps
1: tetrabutyl ammonium fluoride
2: chlorobenzene / 132 °C
3: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
4: 1,8-diazabicyclo[5.4.0]undec-7-ene
5: Imidazole hydrochloride / 60 °C
View Scheme
C35H59NO12

C35H59NO12

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
2.2: 0.58 h / 23 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
4.1: 12 h / 23 °C / 0.1 Torr
4.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 130 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
2.2: 0.58 h / 23 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
4.1: 12 h / 23 °C / 0.1 Torr
4.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 4 steps
1: chlorobenzene / 132 °C
2: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
3: 1,8-diazabicyclo[5.4.0]undec-7-ene
4: Imidazole hydrochloride / 60 °C
View Scheme
C32H53NO11

C32H53NO11

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
1.2: 0.58 h / 23 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
3.1: 12 h / 23 °C / 0.1 Torr
3.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
2: 1,8-diazabicyclo[5.4.0]undec-7-ene
3: Imidazole hydrochloride / 60 °C
View Scheme
6-((2R,3R,4R,6R)-7-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-4-methoxy-4,6-dimethylheptan-2-yl)-2,2,5-trimethyl-4H-1,3-dioxin-4-one

6-((2R,3R,4R,6R)-7-((tert-butyldiphenylsilyl)oxy)-3-hydroxy-4-methoxy-4,6-dimethylheptan-2-yl)-2,2,5-trimethyl-4H-1,3-dioxin-4-one

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
2.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
3.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7.1: 130 °C
8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
8.2: 0.58 h / 23 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
10.1: 12 h / 23 °C / 0.1 Torr
10.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 10 steps
1.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
2.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
3.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
4.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
5.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
7.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
8.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
8.2: 0.58 h / 23 °C
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
10.1: 12 h / 23 °C / 0.1 Torr
10.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 10 steps
1: silver trifluoromethanesulfonate
2: hydrogen fluoride / water
3: Dess-Martin periodane
4: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
5: Dess-Martin periodane
6: tetrabutyl ammonium fluoride
7: chlorobenzene / 132 °C
8: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
9: 1,8-diazabicyclo[5.4.0]undec-7-ene
10: Imidazole hydrochloride / 60 °C
View Scheme
C32H52FNO11

C32H52FNO11

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
2.1: 12 h / 23 °C / 0.1 Torr
2.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 2 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene
2: Imidazole hydrochloride / 60 °C
View Scheme
C51H77NO12Si

C51H77NO12Si

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutyl ammonium fluoride / 130 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
2.2: 0.58 h / 23 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
4.1: 12 h / 23 °C / 0.1 Torr
4.2: 2 h / 45 °C
View Scheme
C43H65NO10Si

C43H65NO10Si

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
2.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6.1: 130 °C
7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
7.2: 0.58 h / 23 °C
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
9.1: 12 h / 23 °C / 0.1 Torr
9.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 9 steps
1.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
2.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
3.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
4.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
6.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
7.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
7.2: 0.58 h / 23 °C
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
9.1: 12 h / 23 °C / 0.1 Torr
9.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 9 steps
1: hydrogen fluoride / water
2: Dess-Martin periodane
3: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
4: Dess-Martin periodane
5: tetrabutyl ammonium fluoride
6: chlorobenzene / 132 °C
7: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
8: 1,8-diazabicyclo[5.4.0]undec-7-ene
9: Imidazole hydrochloride / 60 °C
View Scheme
C27H47NO10

C27H47NO10

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
6.2: 0.58 h / 23 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
8.1: 12 h / 23 °C / 0.1 Torr
8.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 8 steps
1.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
2.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
3.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
5.1: 130 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
6.2: 0.58 h / 23 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
8.1: 12 h / 23 °C / 0.1 Torr
8.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 8 steps
1: Dess-Martin periodane
2: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
3: Dess-Martin periodane
4: tetrabutyl ammonium fluoride
5: chlorobenzene / 132 °C
6: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
7: 1,8-diazabicyclo[5.4.0]undec-7-ene
8: Imidazole hydrochloride / 60 °C
View Scheme
(2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3R,4R,6R)-4-methoxy-4,6-dimethyl-7-oxo-2-(2,2,5-trimethyl-4-oxo-4H-1,3-dioxin-6-yl)heptan-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl methyl carbonate

(2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3R,4R,6R)-4-methoxy-4,6-dimethyl-7-oxo-2-(2,2,5-trimethyl-4-oxo-4H-1,3-dioxin-6-yl)heptan-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl methyl carbonate

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
2.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
4.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
5.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
5.2: 0.58 h / 23 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
7.1: 12 h / 23 °C / 0.1 Torr
7.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 7 steps
1.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
2.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
4.1: 130 °C
5.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
5.2: 0.58 h / 23 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
7.1: 12 h / 23 °C / 0.1 Torr
7.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 7 steps
1: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
2: Dess-Martin periodane
3: tetrabutyl ammonium fluoride
4: chlorobenzene / 132 °C
5: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
6: 1,8-diazabicyclo[5.4.0]undec-7-ene
7: Imidazole hydrochloride / 60 °C
View Scheme
tert-butyl 2-methyl-3-oxopentanoate
26735-86-4

tert-butyl 2-methyl-3-oxopentanoate

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: acetic anhydride; sulfuric acid / 5 h / 0 - 20 °C
2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C
2.2: 3 h / -78 - 20 °C
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: 130 °C
11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
11.2: 0.58 h / 23 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
13.1: 12 h / 23 °C / 0.1 Torr
13.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 13 steps
1.1: acetic anhydride; sulfuric acid / 5 h / 0 - 20 °C
2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / -78 - 0 °C
2.2: 3 h / -78 - 20 °C
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
11.2: 0.58 h / 23 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
13.1: 12 h / 23 °C / 0.1 Torr
13.2: 2 h / 45 °C
View Scheme
(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylpentan-2-ol

(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-methylpentan-2-ol

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: potassium hydride / diethyl ether; mineral oil / 1 h / 0 °C
1.2: 2 h / 20 °C
2.1: periodic acid / ethyl acetate
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: 130 °C
11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
11.2: 0.58 h / 23 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
13.1: 12 h / 23 °C / 0.1 Torr
13.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 13 steps
1.1: potassium hydride / diethyl ether; mineral oil / 1 h / 0 °C
1.2: 2 h / 20 °C
2.1: periodic acid / ethyl acetate
3.1: magnesium bromide ethyl etherate / dichloromethane / 0.17 h / -78 - -10 °C
3.2: 12 h / -78 °C
4.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 1 h / 0 °C / Molecular sieve
5.1: hydrogen fluoride / acetonitrile / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane; water / 0.5 h / 20 °C
7.1: bis(cyclopentadienyl)titanium dichloride; 2-methylpropylmagnesium chloride
8.1: Dess-Martin periodane / dichloromethane; water / 0.08 h / 22 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 23 °C
10.1: chlorobenzene / 19.17 h / 23 - 150 °C / Inert atmosphere; Sonication
11.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / -78 °C
11.2: 0.58 h / 23 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / -10 °C
13.1: 12 h / 23 °C / 0.1 Torr
13.2: 2 h / 45 °C
View Scheme
Multi-step reaction with 13 steps
1: potassium hydride
2: periodic acid
3: zinc(II) chloride
4: silver trifluoromethanesulfonate
5: hydrogen fluoride / water
6: Dess-Martin periodane
7: bis(cyclopentadienyl)titanium dichloride; cyclopentylmagnesium bromide
8: Dess-Martin periodane
9: tetrabutyl ammonium fluoride
10: chlorobenzene / 132 °C
11: potassium tert-butylate; N-fluorobis(benzenesulfon)imide
12: 1,8-diazabicyclo[5.4.0]undec-7-ene
13: Imidazole hydrochloride / 60 °C
View Scheme
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

C42H63FN6O10

C42H63FN6O10

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate In dichloromethane at 20℃; for 24h;20%
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

C103H122N10O20S

C103H122N10O20S

trifluoroacetic acid
76-05-1

trifluoroacetic acid

A

C146H185FN16O29S*C2HF3O2

C146H185FN16O29S*C2HF3O2

B

C146H185FN16O29S*C2HF3O2

C146H185FN16O29S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone; C103H122N10O20S With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;
Stage #2: trifluoroacetic acid In water; acetonitrile
A 16%
B 12%
(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone
760981-83-7

(3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone

C103H122N10O20S

C103H122N10O20S

trifluoroacetic acid
76-05-1

trifluoroacetic acid

A

C146H185FN16O29S*C2HF3O2

C146H185FN16O29S*C2HF3O2

B

C146H185FN16O29S*C2HF3O2

C146H185FN16O29S*C2HF3O2

Conditions
ConditionsYield
Stage #1: (3aS,4R,7S,9R,10R,11R,13R,15R)-1-(4-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)butyl)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-7-fluoro-11-methoxy-3a,7,9,11,13,15-hexamethyloctahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(7H,9H)-tetraone; C103H122N10O20S With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;
Stage #2: trifluoroacetic acid In water-d2; acetonitrile
A 12%
B 13%

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