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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product s

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone Manufacturer/High quality/Best price/In stock

Cas:13096-62-3

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality 2,3,4,6-Tetra-O-Benzyl-D-Glucono-1,5-Lactone supplier in China

Cas:13096-62-3

Min.Order:1 Metric Ton

Negotiable

Type:Manufacturers

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Wuhan Fortuna Chemical Co.,Ltd

Manufacturer supply 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone CAS 13096-62-3 with superior quality Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical &a

Manufacturer supply 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone CAS 13096-62-3 with superior quality

Cas:13096-62-3

Min.Order:10 Kilogram

FOB Price: $10.0

Type:Trading Company

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Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

Cangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

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ANQING CHICO PHARMACEUTICAL CO.,LTD.

High quality. Factory supply. In stock. Best price.1.Quick response within 24 hours;2.Best quality in your requirement;?3.We pay more attention on delivery time, and usually ship on time;4.Under the premise of safety and effectiveness, we can produce

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Trading Company

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Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

2,3,4,6-Tetrakis-O-(phenylmethyl)-D-gluconic acid lactone

Cas:13096-62-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.

TIANFU CHEM 2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:100 Gram

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

Factory direct supply CAS 13096-62-3 with best quality

Cas:13096-62-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone CAS No.:13096-62-3 HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on the mar

High purity 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone CAS No.:13096-62-3

Cas:13096-62-3

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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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

D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone 13096-62-3

Cas:13096-62-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Shanghai Minstar Chemical Co., Ltd

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE Basic information Product Name: 2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE Synonyms: 2,3,4,6-TETRAKIS-O-(PHENYLMETHYL)-D-GLUCONIC ACID LACTONE;2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE;5-lactone

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:100 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE CAS:13096-62-3 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

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE CAS:13096-62-3

Cas:13096-62-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Triumph International Development Limilted

Lorcaserin(856681-05-5)is an orally administered agent and a selective 5-HT2C receptor agonist for the treatment of obesity. It had been approved for marketing in US by FDA on 27 June in 2012. In clinical studies, lorcaserin h

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:100 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

NewCan Biotech Limited

NewCan Biotech Limited was established in 2021 and is primarily engaged in the research, development, production, and sales of sugars, nucleosides, nucleotides, phosphorylated monomers, as well as next-generation antiviral and antitumor drug intermed

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:1 Milligram

Negotiable

Type:Trading Company

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Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

2,3,4,6,-tetra-o-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

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

2,3,4,6-Tetra-o-benzyl-d-glucono-1,5-lactone CAS NO.13096-62-3

Cas:13096-62-3

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONEAppearance:as detail Storage:Room temperature Package:according to customers' requirements Application:Pharmaceutical Intermediates Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB or

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Siwei Development Group Ltd.

Product name: 2,3,4,6-Tetra-O-Benzyl-D-Glucono-1,5-Lactone CAS No.: 13096-62-3 Molecule Formula:C34H34O6 Molecule Weight:538.63 Purity: 97.0% Package: 5kg/drum Description:White or off-white powder Manufacture Standards:Enterprise Standard

Lower Price 2,3,4,6-Tetra-O-Benzyl-D-Glucono-1,5-Lactone on stock

Cas:13096-62-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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,

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Jiangsu Qianyu Molecular Technology Co., LTD.

Our Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an

Quality Manufacturer 2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Hunan chemfish Pharmaceutical co.,Ltd

Hunan chemfish Pharmaceutical co.,Ltd.located in Lugu High-tech industral park ,Hunan province . with its own R&D center and more than 10000㎡manufacture plant . Chemfish owns 40 reactors from 1000L to 8000L. With complete auxiliary equipment as

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Hangzhou Huarong Pharm Co., Ltd.

We Huarong Pharm can provide Customized Synthesis & Process R&D & APIs and intermediates Production & Quality Research & Registration Application, especially our GMP validation service which complies with SFDA, FDA, WHO and EU EMPA. O

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

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

D-Gluconic acid,2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone

Cas:13096-62-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Golden Pharma Co., Limited

GOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

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

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Win-Win chemical Co.Ltd

Stock products, own laboratory Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:Shanghai

2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone cas no. 13096-62-3 98%

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Kono Chem Co.,Ltd

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou

2,3,4,6-TETRA-O-BENZYL-D-GLUCONO-1,5-LACTONE

Cas:13096-62-3

Min.Order:0

Negotiable

Type:Other

inquiry

Hangzhou Dingyan Chem Co., Ltd

R & D enterprises have their own stock in stockAppearance:To be subject to the object Package:Customized Application:pharmaceutical intermediates Transportation:Air Port:Shanghai;Guangzhou

Synthetic route

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Solvent;100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;100%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h;100%
2,3,4,6-tetra-O-benzyl-D-glucopyranoside
59531-24-7

2,3,4,6-tetra-O-benzyl-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With acetic anhydride; dimethyl sulfoxide at 20℃;93%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside In dimethyl sulfoxide at 20 - 25℃; for 0.5h; Inert atmosphere;
Stage #2: With acetic anhydride at 15 - 25℃; Inert atmosphere;
92%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve;
Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h;
82%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranoside With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 105h;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 1h;
2,3,4,6-tetra-O-benzyl-D-glucopyranose
6564-72-3

2,3,4,6-tetra-O-benzyl-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With acetic anhydride In dimethyl sulfoxide at 20℃;89%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve;
Stage #2: With tetrapropylammonium perruthenate In dichloromethane at 20℃; for 2h;
82%
Stage #1: 2,3,4,6-tetra-O-benzyl-D-glucopyranose With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333h; Molecular sieve;
Stage #2: tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h;
82%
(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide
128984-82-7

(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Amberlite IR 120 H+ In 1,4-dioxane for 3h; Heating;88%
2,3,4,6-tetra-O-benzoyl-D-glucopyranose
627466-64-2

2,3,4,6-tetra-O-benzoyl-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Oxidation;85%
1-O-allyloxycarbonyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

1-O-allyloxycarbonyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With palladium diacetate In acetonitrile at 80℃; for 2h;60%
phenacyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

phenacyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

(3R,4S,6R,7R,8S,9R)-7,8,9-Tris-benzyloxy-6-benzyloxymethyl-3-phenyl-1,5-dioxa-spiro[3.5]nonan-3-ol

(3R,4S,6R,7R,8S,9R)-7,8,9-Tris-benzyloxy-6-benzyloxymethyl-3-phenyl-1,5-dioxa-spiro[3.5]nonan-3-ol

Conditions
ConditionsYield
In benzene for 5h; Ambient temperature; Irradiation;A 57%
B 24%
phenacyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
172986-43-5

phenacyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

(3R,4S,6R,7R,8S,9R)-7,8,9-Tris-benzyloxy-6-benzyloxymethyl-3-phenyl-1,5-dioxa-spiro[3.5]nonan-3-ol

(3R,4S,6R,7R,8S,9R)-7,8,9-Tris-benzyloxy-6-benzyloxymethyl-3-phenyl-1,5-dioxa-spiro[3.5]nonan-3-ol

Conditions
ConditionsYield
In benzene for 5h; Ambient temperature; Irradiation;A 56%
B 20%
1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-tert-butyl sulfinothioate

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-tert-butyl sulfinothioate

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
118206-39-6

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Conditions
ConditionsYield
In toluene at 110℃; Inert atmosphere;A 45%
B 45%
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone
82598-88-7

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
62641-00-3

<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone

Conditions
ConditionsYield
With magnesium iodide In ethanol at 20℃; for 1h;A 35%
B 5%
2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose
154127-55-6

2,3,4,6-tetra-O-benzyl-β-1-C-(2-thiazolyl)-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 4 A molecular sieve In toluene at 130℃; for 14h; closed vial; Yield given;
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(5R,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1-methyl-4-oxa-1,2-diaza-spiro[2.5]octane

(5R,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1-methyl-4-oxa-1,2-diaza-spiro[2.5]octane

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

1'-methyl-2'-[(Z)-2,3,4,6-tetra-O-benzyl-D-glucopyranosyllidene]toluene-4-sulfohydrazide

1'-methyl-2'-[(Z)-2,3,4,6-tetra-O-benzyl-D-glucopyranosyllidene]toluene-4-sulfohydrazide

Conditions
ConditionsYield
With pyridine In dichloromethane for 3.5h; Title compound not separated from byproducts;
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TfOH / H2O
2: DMSO / acetic anhydride
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C
2: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; hydrogenchloride / water / 85 °C
2: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; sulfuric acid / Reflux
2: acetic anhydride; dimethyl sulfoxide / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; sulfuric acid / water / 2 h / Reflux
2: acetic anhydride / dimethyl sulfoxide / 20 °C
View Scheme
methyl-alpha-D-glucopyranoside
97-30-3

methyl-alpha-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; acetic acid / water / 6 h / Reflux
2: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C
3.1: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
1.2: 18 h / 20 °C / Inert atmosphere
2.1: acetic acid; hydrogenchloride / water / 85 °C
3.1: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: methanol; sodium methylate / 20 °C
2.2: Amberlite.(R). IR-120 H+ ion exchange
3.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere
3.2: 12 h / 20 °C / Inert atmosphere
4.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C
5.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 0 - 20 °C
2: sodium methylate; methanol
3: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
4: N-iodo-succinimide; water / acetone
5: acetic anhydride; dimethyl sulfoxide / 20 °C
View Scheme
phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside
38184-10-0

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C
2: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C
View Scheme
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol
2936-70-1, 5624-48-6, 13992-15-9, 16758-34-2, 28244-97-5, 77481-62-0, 77481-63-1, 105088-17-3, 149495-84-1

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere
1.2: 12 h / 20 °C / Inert atmosphere
2.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C
3.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C
View Scheme
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
13992-16-0, 23661-28-1, 24404-53-3, 28512-68-7, 65236-85-3, 86782-39-0, 108032-93-5, 121524-01-4, 121570-34-1

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: methanol; sodium methylate / 20 °C
1.2: Amberlite.(R). IR-120 H+ ion exchange
2.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere
2.2: 12 h / 20 °C / Inert atmosphere
3.1: N-Bromosuccinimide; water / acetone / 3 h / 20 °C
4.1: acetic anhydride; dimethyl sulfoxide / 12 h / 30 °C
View Scheme
2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran
6207-45-0, 60478-61-7, 112344-80-6, 126924-14-9, 6207-44-9

2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.25 h / 70 °C
1.2: 2 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C
2.2: -78 - 0 °C
View Scheme
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium methylate; methanol
2: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
3: N-iodo-succinimide; water / acetone
4: acetic anhydride; dimethyl sulfoxide / 20 °C
View Scheme
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
2: N-iodo-succinimide; water / acetone
3: acetic anhydride; dimethyl sulfoxide / 20 °C
View Scheme
phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside
91602-61-8, 38184-10-0, 62774-37-2, 74801-29-9, 116501-52-1, 116501-53-2, 139974-84-8

phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-iodo-succinimide; water / acetone
2: acetic anhydride; dimethyl sulfoxide / 20 °C
View Scheme
methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
84799-77-9

methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; water; sulfuric acid / 1 h / 110 °C
2: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; acetic acid / water / 5 h / 100 °C / Inert atmosphere
2: pyridinium chlorochromate / dichloromethane / 48 h / 20 °C / Inert atmosphere; Molecular sieve
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere
1.2: 20 h / 20 °C / Inert atmosphere
2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C
3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: tetrahydrofuran / 0.33 h / 55 °C
2: hydrogenchloride / tetrahydrofuran / 0.25 h / 20 °C
3: sodium hydroxide; dihydrogen peroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0.17 h / 65 °C
View Scheme
benzyl bromide
100-39-0

benzyl bromide

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere
1.2: 20 h / 20 °C / Inert atmosphere
2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C
3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
1.2: 0 - 20 °C
2.1: hydrogenchloride; strontium (III) chloride hexahydrate / acetic acid; water / 70 °C
3.1: caesium carbonate; Iodine monochloride / dichloromethane / 3 h / 0 - 20 °C / Green chemistry
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
1.2: 18 h / 20 °C / Inert atmosphere
2.1: acetic acid; hydrogenchloride / water / 85 °C
3.1: acetic anhydride / dimethyl sulfoxide / 22 h / 20 °C / Inert atmosphere
View Scheme
(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol
72174-24-4, 53269-97-9

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
118206-39-6

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
2: toluene / 110 °C / Inert atmosphere
View Scheme
O-ethyl S-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl) dithiocarbonate
53269-96-8, 116429-58-4, 116429-59-5, 130738-70-4, 141561-28-6

O-ethyl S-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl) dithiocarbonate

A

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

B

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
118206-39-6

2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium / methanol / 2 h / 20 °C
2: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
3: toluene / 110 °C / Inert atmosphere
View Scheme
benzyl chloride
100-44-7

benzyl chloride

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 0.33 h / 55 °C
2: hydrogenchloride / tetrahydrofuran / 0.25 h / 20 °C
3: sodium hydroxide; dihydrogen peroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water / 0.17 h / 65 °C
View Scheme
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-1-C-butyl-D-glucopyranose

2,3,4,6-tetra-O-benzyl-1-C-butyl-D-glucopyranose

Conditions
ConditionsYield
at -78℃;100%
In tetrahydrofuran; toluene at -50℃; for 2h;72%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

phenyllithium
591-51-5

phenyllithium

(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose
118436-89-8, 118436-90-1

(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose

Conditions
ConditionsYield
at -78℃;100%
In tetrahydrofuran 1.) -78 deg C, 2 h, 2.) from -78 deg C to room temperature, 2 h;85.7%
In tetrahydrofuran at -78℃;
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(3-methylindol-1-yl)magnesium bromide

(3-methylindol-1-yl)magnesium bromide

(2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-1-(3-methyl-indol-1-yl)-hexan-1-one

(2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-1-(3-methyl-indol-1-yl)-hexan-1-one

Conditions
ConditionsYield
In tetrahydrofuran; toluene at -20℃;100%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(3R,4S,5R,6R)-3,4,5-trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-ethylbenzo[b]thiophen-2-yl-methyl)naphthalen-1-yl]tetrahydropyran-2-ol
874357-34-3

(3R,4S,5R,6R)-3,4,5-trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-ethylbenzo[b]thiophen-2-yl-methyl)naphthalen-1-yl]tetrahydropyran-2-ol

Conditions
ConditionsYield
Stage #1: 2-(4-bromo-naphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 0.0833333h;
100%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane
655237-57-3

((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane

2,3,4,6-tetra-O-benzyl-1-C-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-D-glucopyranose

2,3,4,6-tetra-O-benzyl-1-C-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-D-glucopyranose

Conditions
ConditionsYield
Stage #1: ((3-bromo-4-fluorobenzyl)oxy)(tert-butyl)dimethylsilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 1h;
100%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene
1030825-20-7

2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-2-ol

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-2-ol

Conditions
ConditionsYield
Stage #1: 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 20℃; for 3h;
99%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

1,3,5-trifluorobenzene
372-38-3

1,3,5-trifluorobenzene

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(2,4,6-trifluorophenyl)tetrahydro-2H-pyran-2-ol

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(2,4,6-trifluorophenyl)tetrahydro-2H-pyran-2-ol

Conditions
ConditionsYield
Stage #1: 1,3,5-trifluorobenzene With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In diethyl ether at -78℃; for 0.25h; Inert atmosphere;
Stage #3: With acetic acid In diethyl ether at -78℃; for 0.166667h; Inert atmosphere;
98%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-D-gluconamide
76670-93-4

2,3,4,6-tetra-O-benzyl-D-gluconamide

Conditions
ConditionsYield
With ammonia In methanol at 0℃; for 2h;97%
With ammonia In methanol96%
With ammonia In methanol at 0℃; for 3h;96%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

trans-2-propenyl bromide
590-15-8

trans-2-propenyl bromide

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-prop-1-ynyl-tetrahydro-pyran-2-ol

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-prop-1-ynyl-tetrahydro-pyran-2-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;97%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

propylene glycol
57-55-6

propylene glycol

1,2-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-1,2-propanediol
77855-88-0, 77881-86-8

1,2-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-1,2-propanediol

Conditions
ConditionsYield
With sulfuric acid In benzene for 24h; Heating;96.2%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

O-(tert-butyl)hydroxylamine hydrochloride

O-(tert-butyl)hydroxylamine hydrochloride

1N-tert-butoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

1N-tert-butoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions
ConditionsYield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;96%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
62641-00-3

<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone

Conditions
ConditionsYield
With sodium hydride; acetophenone In tetrahydrofuran 1.) 45 deg C, 30 min, 2.) 25 deg C, 5 min.;95%
With sodium methylate In methanol for 0.5h; Ambient temperature;40 mg
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose
140926-87-0

3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 1h;95%
With n-butyllithium92%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.333333h; Metallation;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -70 - -40℃; for 1h; Addition;
91%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78 - 0℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate cooling with ice;
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

tert-butyl 2-(bromomethyl)acrylate
53913-96-5

tert-butyl 2-(bromomethyl)acrylate

2-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-ylmethyl)-acrylic acid tert-butyl ester

2-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-ylmethyl)-acrylic acid tert-butyl ester

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃;95%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

1N-methoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

1N-methoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions
ConditionsYield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;95%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

ethyl acetate
141-78-6

ethyl acetate

2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate
132470-52-1

2-deoxy-4,5,6,8-tetra-O-benzyl-α-D-gluco-3,7-pyranoso-3-octulosonate

Conditions
ConditionsYield
With lithium hexamethyldisilazane95%
Stage #1: ethyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.25h;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Further stages.;
66%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
389121-73-7

1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Conditions
ConditionsYield
95%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

phenylmagnesium bromide
1589-82-8

phenylmagnesium bromide

1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
389121-73-7

1-C-benzyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78 - -40℃; for 2h;95%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-1-C-n-butyl-α-D-glucopyranose
292149-85-0

2,3,4,6-tetra-O-benzyl-1-C-n-butyl-α-D-glucopyranose

Conditions
ConditionsYield
Stage #1: n-butyllithium; (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: With water In tetrahydrofuran; hexane Further stages.;
95%
In tetrahydrofuran; hexane at -78℃; for 0.5h; diastereoselective reaction;92%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

allyl bromide
106-95-6

allyl bromide

(3R,4S,5R,6R)-2,2-diallyl-3,4,5-tris(benzyloxy)-6-(benzyloxy)methyltetrahydropyran

(3R,4S,5R,6R)-2,2-diallyl-3,4,5-tris(benzyloxy)-6-(benzyloxy)methyltetrahydropyran

Conditions
ConditionsYield
With chloro-trimethyl-silane; zinc In tetrahydrofuran at 20℃; for 4h; Barbier Coupling Reaction;95%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

dichloromethane
75-09-2

dichloromethane

2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-α-D-glucopyranose
140658-50-0

2,3,4,6-Tetra-O-benzyl-1-C-(dichloromethyl)-α-D-glucopyranose

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -75 - -70℃; for 1h;94%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,2-Dimethyl-1,3-propanediol
126-30-7

2,2-Dimethyl-1,3-propanediol

2,3,4,6-tetra-O-benzyl-5',5'-dimethylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxane]
261713-59-1

2,3,4,6-tetra-O-benzyl-5',5'-dimethylspiro[1,5-anhydro-D-glucitol-1,2'-[1,3]dioxane]

Conditions
ConditionsYield
With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 1h;94%
With Trimethylmethoxysilane; trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 2h; Cycloaddition;94%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

methyllithium
917-54-4

methyllithium

3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose
137344-41-3

3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; diastereoselective reaction;94%
In tetrahydrofuran; diethyl ether at -78℃; for 1h;83%
In tetrahydrofuran at -78℃; for 0.166667h;67%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Cp2TiMe2

Cp2TiMe2

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
133697-34-4, 97321-70-5

2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Conditions
ConditionsYield
In toluene94%
In toluene at 65 - 70℃; for 14h;
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside
89160-10-1

methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-2-ol

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-2-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -50℃;93%
With n-butyllithium In tetrahydrofuran at -50℃; for 1h;92%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

N-benzyloxyamine
622-33-3

N-benzyloxyamine

1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide
270062-18-5

1N-benzyloxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions
ConditionsYield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;93%
Stage #1: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; N-benzyloxyamine In dichloromethane at 20℃; for 0.5h;
Stage #2: With trimethylaluminum In hexane; dichloromethane at 20℃; for 1h; Further stages.;
93%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

O-ethylhydroxylamine hydrochloride
3332-29-4

O-ethylhydroxylamine hydrochloride

1N-ethoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

1N-ethoxy-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-(2R,3S,4R,5R)-hexanamide

Conditions
ConditionsYield
With trimethylaluminum In dichloromethane at 20℃; for 1h; Alkoxyamination;93%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

tert-butyl 4-iodobenzoate
120363-13-5

tert-butyl 4-iodobenzoate

1-C-(4-tert-butoxycarbonylphenyl)-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

1-C-(4-tert-butoxycarbonylphenyl)-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Conditions
ConditionsYield
With n-butyllithium; 2,4,6-triisopropyl-1-bromobenzene In tetrahydrofuran at -78℃; for 1h; Reagent/catalyst; Barbier Coupling Reaction; Inert atmosphere; stereoselective reaction;93%
Stage #1: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; tert-butyl 4-iodobenzoate With 2,4,6-triisopropylphenyl lithium In tetrahydrofuran at -78℃;
Stage #2: With ammonium chloride In water
93%

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