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Hebei Mojin Biotechnology Co.,Ltd

Company information: Hebei Mojin Biotechnology Co., Ltd, Our company is a professional in chemical raw materials and chemical reagents research and development production enterprises. Our business covers more than 30 countries, most of the big custo

In stock low price Spinosad CAS 131929-60-7

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $20.0 / 30.0

Type:Trading Company

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Wuhan ZeShanCheng Biomedical Technology Co., Ltd.

1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists

SpinosadA

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $480.0 / 500.0

Type:Trading Company

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Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Assay 98%min ----------------------------------------------------------------------------------------------

High purity Various Specifications spinosad CAS:131929-60-7

Cas:131929-60-7

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Trading Company

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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 CMO

SPINOSAD manufacturer/supplier

Cas:131929-60-7

Min.Order:1 Gram

Negotiable

Type:Manufacturers

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Wuhan Fortuna Chemical Co.,Ltd

Unique advantages Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White crystalline powder Storage:cool dry place Package:1kg/foil bag;25kg/drum Application:veterinary medicine raw

Manufacturer high quality Spinosad Cas 131929-60-7 with good price

Cas:131929-60-7

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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Xi'an Quanao Biotech Co., Ltd.

Xi’an Quanao Biotech Co., Ltd. with 18 years experience in plant extract filed. Product grade: Medicine, Health care product, Cosmetics, Food, Beverage, Feed. Hot selling market: Europe, North America, South America, Middle East, Asia Pacifi

Pesticides Powder 99% Spinosad Price cas:131929-60-7

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $39.0 / 49.0

Type:Manufacturers

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Henan Allgreen Chemical Co.,Ltd

high quality Appearance:white or off white powder Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai

SPINOSAD

Cas:131929-60-7

Min.Order:1 Kilogram

Negotiable

Type:Manufacturers

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Hangzhou Think Chemical Co. Ltd

Spinosad CAS:131929-60-7 Synonyms Spinosyn A; 2-{(6-Deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy}-13-{{5-(dimethylamino)tetr ahydro-6-methyl-2H-pyran-2-yl}oxy}-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-t etradecahydr

Spinosad stock with the competitive price and good quality

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem’s 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. Near 20 years DayangChem has provided dif

Spinosyn A

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

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Hebei yanxi chemical co.,LTD.

Hebei Yanxi Chemical Co., Ltd. is a professional research, development and production of lead acetate benzene acetamide enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low car

SPINOSAD

Cas:131929-60-7

Min.Order:1 Metric Ton

FOB Price: $1.0 / 2.0

Type:Trading Company

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Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

SPINOSAD CAS 131929-60-7

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

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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

Manufacturer supply CAS 131929-60-7 with competitive price

Cas:131929-60-7

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Spinosad Veterinary API/high quality/lower price

Cas:131929-60-7

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages ♦ High purity, all above 98.5%, no impurities after dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available ♦ W

SPINOSAD CAS131929-60-7

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $7.0 / 9.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Product Name: Spinosyn D Synonyms: spinosad CAS: 131929-60-7 MF: C41H65NO10 MW: 731.956 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:25

Spinosyn D

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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HANWAYS CHEMPHARM CO.,LIMITED

Hanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr

Bulk Spinosad powder 99% insecticides spinosad CAS: 131929-60-7 in stock Fast Delivery

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $20.0 / 40.0

Type:Trading Company

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Shanghai Upbio Tech Co.,Ltd

product Name: SPINOSAD Molecular Weight: 731.96 Density: 1.16 g/cm3 Boiling Point: 801.5 °C at 760 mmHg Melting Point: 84 C to 99.5 C Flash Point: 438.5 °C Refractive index: 1.54 Solubility: Water = 89.4 ppm (Spinosyn A) 0.495

High quality SPINOSAD CAS131929-60-7

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $10.0

Type:Lab/Research institutions

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Baoji Guokang Healthchem co.,ltd

About us 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.

SPINOSAD

Cas:131929-60-7

Min.Order:1 Kilogram

FOB Price: $180.0 / 200.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

SPINOSAD CAS:131929-60-7 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,

SPINOSAD CAS:131929-60-7

Cas:131929-60-7

Min.Order:1 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

LIDE PHARMACEUTICALS LIMITED

Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&amp

Wuhan Wonda Pharm Limited

1.High Quality: Quality is life. Quality is the most important element for all goods. We have a lab doing research in Wuhan China and produce sarms in bulk quantity. We have 8 years experience making all kinds of sarms. And all our old customers

High Efficiency And Pollution-free Spinosad CAS 131929-60-7

Cas:131929-60-7

Min.Order:1 Gram

Negotiable

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

Hangzhou Fandachem Co.,Ltd

Hangzhou Fanda Chemical Co.,Ltd (FandaChem) , a China-based chemical company, specialize in exporting Spinosyn A cas: 131929-60-7, Please contact us by email freely. We are leading exporter in China. If you really need this cargo, ple

Spinosyn A cas: 131929-60-7 from FandaChem

Cas:131929-60-7

Min.Order:1 Metric Ton

Negotiable

Type:Other

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Triumph International Development Limilted

Appearance:white powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:Common products:Sea/Air/Courie

spinosad

Cas:131929-60-7

Min.Order:100 Metric Ton

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 Pharmaceutical acti

Buy Quality Spinosad 131929-60-7 Crystaline On Hot Sale

Cas:131929-60-7

Min.Order:1 Gram

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-

Spinosad Factor A 131929-60-7

Cas:131929-60-7

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

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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

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 SPINOSAD

Cas:131929-60-7

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

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Henan Tianfu Chemical Co., Ltd.

SPINOSAD Basic information Product Name: SPINOSAD Synonyms: SPINOSAD;(2r-(2r*,3as*,5ar*,5bs*,9s*,13s*(2r*,5s*,6r*),14r*,16as*,16br*))-ethyl;)oxy)-13-((5-dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl)oxy)-9-ethyl-14-m;1h-as-indaceno(3,2-d)oxacyc

131929-60-7 SPINOSAD

Cas:131929-60-7

Min.Order:1 Metric Ton

Negotiable

Type:Lab/Research institutions

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Synthetic route

Dimethyl-[(2R,3S)-2-methyl-6-(pyrimidin-2-ylsulfanyl)-tetrahydro-pyran-3-yl]-amine

Dimethyl-[(2R,3S)-2-methyl-6-(pyrimidin-2-ylsulfanyl)-tetrahydro-pyran-3-yl]-amine

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione
131929-68-5

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione

A

spinosyn A
131929-60-7

spinosyn A

B

C41H65NO10

C41H65NO10

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane for 3h; Yield given. Yields of byproduct given;
methyl 4-formylbutanoate
6026-86-4

methyl 4-formylbutanoate

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: (-)-(1S,2R)-N,N-dibutylnorephedrine / hexane; toluene / 72 h / 0 °C
2: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
3: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
4: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
5: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
6: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
7: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
8: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
9: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
10: Jones reagent / acetone / 1.5 h / 0 °C
11: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
12: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
13: 63 percent / methanolic K2CO3 / 48 h / Heating
14: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
15: 91 percent / 49percent aq. HF / acetonitrile / 24 h
16: AgOTf3 / CH2Cl2 / 3 h
View Scheme
D-forosamine
56587-30-5

D-forosamine

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) diethyl azodicarboxylate, PPh3 / 1.) THF, -50 deg C, 10 min, 2.) THF, from -50 to 20 deg C, 3 h
2: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(S)-5-Hydroxy-heptanoic acid methyl ester
118545-01-0

(S)-5-Hydroxy-heptanoic acid methyl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
2: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
3: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
4: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
5: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
6: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
7: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
8: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
9: Jones reagent / acetone / 1.5 h / 0 °C
10: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
11: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
12: 63 percent / methanolic K2CO3 / 48 h / Heating
13: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
14: 91 percent / 49percent aq. HF / acetonitrile / 24 h
15: AgOTf3 / CH2Cl2 / 3 h
View Scheme
13,14β-Dihydro A83543A aglycon 9α,17α-bis-O-(TBDMS) ether
155189-82-5

13,14β-Dihydro A83543A aglycon 9α,17α-bis-O-(TBDMS) ether

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1: t-BuOOH, Triton B / methanol; H2O; tetrahydrofuran / 120 h / Ambient temperature
2: diethyl ether / 0 °C
3: 87 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature
4: 85 percent / NaIO4 / tetrahydrofuran; H2O / Ambient temperature
5: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
6: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
7: 90 percent / pyridine, DMAP
8: MeOH / 168 h / Heating
9: camphorsulfonic acid / CH2Cl2 / 24 h
10: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
11: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
12: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
13: Jones reagent / acetone / 1.5 h / 0 °C
14: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
15: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
16: 63 percent / methanolic K2CO3 / 48 h / Heating
17: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
18: 91 percent / 49percent aq. HF / acetonitrile / 24 h
19: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(S)-5-(tert-butyldimethylsiloxy)heptanal
204381-35-1

(S)-5-(tert-butyldimethylsiloxy)heptanal

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
2: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
3: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
4: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
5: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
6: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
7: Jones reagent / acetone / 1.5 h / 0 °C
8: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
9: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
10: 63 percent / methanolic K2CO3 / 48 h / Heating
11: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
12: 91 percent / 49percent aq. HF / acetonitrile / 24 h
13: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(S)-5-(tert-Butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester
204381-34-0

(S)-5-(tert-Butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
2: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
3: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
4: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
5: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
6: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
7: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
8: Jones reagent / acetone / 1.5 h / 0 °C
9: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
10: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
11: 63 percent / methanolic K2CO3 / 48 h / Heating
12: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
13: 91 percent / 49percent aq. HF / acetonitrile / 24 h
14: AgOTf3 / CH2Cl2 / 3 h
View Scheme
Formic acid 2-((3S,3aR,5aS,7R,8aR,8bS)-7-hydroxy-2-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl)-ethyl ester
204381-32-8

Formic acid 2-((3S,3aR,5aS,7R,8aR,8bS)-7-hydroxy-2-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl)-ethyl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 90 percent / pyridine, DMAP
2: MeOH / 168 h / Heating
3: camphorsulfonic acid / CH2Cl2 / 24 h
4: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
5: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
6: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
7: Jones reagent / acetone / 1.5 h / 0 °C
8: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
9: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
10: 63 percent / methanolic K2CO3 / 48 h / Heating
11: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
12: 91 percent / 49percent aq. HF / acetonitrile / 24 h
13: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(2R,3aS,5aR,5bS,10aS,10bR)-2-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,5a,5b,6,7,9,9a,10,10a,10b-dodecahydro-1H-8-oxa-cyclopenta[a]fluoren-9-ol
204381-30-6

(2R,3aS,5aR,5bS,10aS,10bR)-2-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,5a,5b,6,7,9,9a,10,10a,10b-dodecahydro-1H-8-oxa-cyclopenta[a]fluoren-9-ol

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
2: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
3: 90 percent / pyridine, DMAP
4: MeOH / 168 h / Heating
5: camphorsulfonic acid / CH2Cl2 / 24 h
6: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
7: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
8: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
9: Jones reagent / acetone / 1.5 h / 0 °C
10: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
11: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
12: 63 percent / methanolic K2CO3 / 48 h / Heating
13: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
14: 91 percent / 49percent aq. HF / acetonitrile / 24 h
15: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-(2-hydroxy-ethyl)-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-(2-hydroxy-ethyl)-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: camphorsulfonic acid / CH2Cl2 / 24 h
2: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
3: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
4: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
5: Jones reagent / acetone / 1.5 h / 0 °C
6: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
7: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
8: 63 percent / methanolic K2CO3 / 48 h / Heating
9: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
10: 91 percent / 49percent aq. HF / acetonitrile / 24 h
11: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-(2-formyloxy-ethyl)-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester
204381-33-9

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-(2-formyloxy-ethyl)-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: MeOH / 168 h / Heating
2: camphorsulfonic acid / CH2Cl2 / 24 h
3: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
4: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
5: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
6: Jones reagent / acetone / 1.5 h / 0 °C
7: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
8: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
9: 63 percent / methanolic K2CO3 / 48 h / Heating
10: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
11: 91 percent / 49percent aq. HF / acetonitrile / 24 h
12: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(R)-3-[(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-isopropyl-oxazolidin-2-one
204381-36-2

(R)-3-[(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-isopropyl-oxazolidin-2-one

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
2: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
3: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
4: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
5: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
6: Jones reagent / acetone / 1.5 h / 0 °C
7: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
8: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
9: 63 percent / methanolic K2CO3 / 48 h / Heating
10: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
11: 91 percent / 49percent aq. HF / acetonitrile / 24 h
12: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(S)-1-[(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(2-hydroxy-ethyl)-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl]-2-methyl-nonane-1,2,7-triol
204519-32-4

(S)-1-[(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(2-hydroxy-ethyl)-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl]-2-methyl-nonane-1,2,7-triol

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: 85 percent / NaIO4 / tetrahydrofuran; H2O / Ambient temperature
2: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
3: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
4: 90 percent / pyridine, DMAP
5: MeOH / 168 h / Heating
6: camphorsulfonic acid / CH2Cl2 / 24 h
7: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
8: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
9: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
10: Jones reagent / acetone / 1.5 h / 0 °C
11: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
12: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
13: 63 percent / methanolic K2CO3 / 48 h / Heating
14: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
15: 91 percent / 49percent aq. HF / acetonitrile / 24 h
16: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoic acid
204381-37-3

(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoic acid

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
2: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
3: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
4: Jones reagent / acetone / 1.5 h / 0 °C
5: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
6: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
7: 63 percent / methanolic K2CO3 / 48 h / Heating
8: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
9: 91 percent / 49percent aq. HF / acetonitrile / 24 h
10: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl chloride
204381-40-8

(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl chloride

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
2: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
3: Jones reagent / acetone / 1.5 h / 0 °C
4: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
5: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
6: 63 percent / methanolic K2CO3 / 48 h / Heating
7: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
8: 91 percent / 49percent aq. HF / acetonitrile / 24 h
9: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(tert-butyl-dimethyl-silanyloxy)-meth-(E)-ylidene]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacene
204381-31-7

(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(tert-butyl-dimethyl-silanyloxy)-meth-(E)-ylidene]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacene

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
2: 90 percent / pyridine, DMAP
3: MeOH / 168 h / Heating
4: camphorsulfonic acid / CH2Cl2 / 24 h
5: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
6: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
7: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
8: Jones reagent / acetone / 1.5 h / 0 °C
9: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
10: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
11: 63 percent / methanolic K2CO3 / 48 h / Heating
12: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
13: 91 percent / 49percent aq. HF / acetonitrile / 24 h
14: AgOTf3 / CH2Cl2 / 3 h
View Scheme
{(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-[3-((S)-4-hydroxy-hexyl)-2-methyl-oxiranecarbonyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl}-acetic acid

{(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-[3-((S)-4-hydroxy-hexyl)-2-methyl-oxiranecarbonyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl}-acetic acid

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: diethyl ether / 0 °C
2: 87 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature
3: 85 percent / NaIO4 / tetrahydrofuran; H2O / Ambient temperature
4: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
5: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
6: 90 percent / pyridine, DMAP
7: MeOH / 168 h / Heating
8: camphorsulfonic acid / CH2Cl2 / 24 h
9: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
10: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
11: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
12: Jones reagent / acetone / 1.5 h / 0 °C
13: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
14: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
15: 63 percent / methanolic K2CO3 / 48 h / Heating
16: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
17: 91 percent / 49percent aq. HF / acetonitrile / 24 h
18: AgOTf3 / CH2Cl2 / 3 h
View Scheme
{(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-[3-((S)-4-hydroxy-hexyl)-2-methyl-oxiranecarbonyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl}-acetic acid methyl ester

{(3S,3aR,5aS,7R,8aR,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-[3-((S)-4-hydroxy-hexyl)-2-methyl-oxiranecarbonyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl}-acetic acid methyl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: 87 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature
2: 85 percent / NaIO4 / tetrahydrofuran; H2O / Ambient temperature
3: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
4: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
5: 90 percent / pyridine, DMAP
6: MeOH / 168 h / Heating
7: camphorsulfonic acid / CH2Cl2 / 24 h
8: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
9: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
10: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
11: Jones reagent / acetone / 1.5 h / 0 °C
12: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
13: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
14: 63 percent / methanolic K2CO3 / 48 h / Heating
15: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
16: 91 percent / 49percent aq. HF / acetonitrile / 24 h
17: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(R)-3-[(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-4-isopropyl-oxazolidin-2-one

(R)-3-[(2R,3S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-4-isopropyl-oxazolidin-2-one

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
2: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
3: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
4: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
5: Jones reagent / acetone / 1.5 h / 0 °C
6: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
7: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
8: 63 percent / methanolic K2CO3 / 48 h / Heating
9: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
10: 91 percent / 49percent aq. HF / acetonitrile / 24 h
11: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-trifluoromethanesulfonyloxy-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester
204381-38-4

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-trifluoromethanesulfonyloxy-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
2: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
3: Jones reagent / acetone / 1.5 h / 0 °C
4: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
5: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
6: 63 percent / methanolic K2CO3 / 48 h / Heating
7: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
8: 91 percent / 49percent aq. HF / acetonitrile / 24 h
9: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(2R,3S,3aR,5aS,7R,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-7-hydroxy-as-indacene-3-acetic acid κ-lactone
204381-44-2

(2R,3S,3aR,5aS,7R,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-7-hydroxy-as-indacene-3-acetic acid κ-lactone

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
2: 91 percent / 49percent aq. HF / acetonitrile / 24 h
3: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(3S,3aR,5aS,7R,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-3,3a,5a,6,7,8,8a,8b-octahydro-7-hydroxy-as-indacene-3-acetic acid κ-lactone pivalate
204381-43-1

(3S,3aR,5aS,7R,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-3,3a,5a,6,7,8,8a,8b-octahydro-7-hydroxy-as-indacene-3-acetic acid κ-lactone pivalate

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 63 percent / methanolic K2CO3 / 48 h / Heating
2: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
3: 91 percent / 49percent aq. HF / acetonitrile / 24 h
4: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-2-methyl-nonanoyl]-6-carboxymethyl-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-2-methyl-nonanoyl]-6-carboxymethyl-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
2: 63 percent / methanolic K2CO3 / 48 h / Heating
3: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
4: 91 percent / 49percent aq. HF / acetonitrile / 24 h
5: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-(2-hydroxy-ethyl)-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-(2-hydroxy-ethyl)-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Jones reagent / acetone / 1.5 h / 0 °C
2: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
3: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
4: 63 percent / methanolic K2CO3 / 48 h / Heating
5: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
6: 91 percent / 49percent aq. HF / acetonitrile / 24 h
7: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-carboxymethyl-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester
204381-42-0

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-carboxymethyl-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
2: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
3: 63 percent / methanolic K2CO3 / 48 h / Heating
4: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
5: 91 percent / 49percent aq. HF / acetonitrile / 24 h
6: AgOTf3 / CH2Cl2 / 3 h
View Scheme
(3S,3aR,5aS,7S,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-7-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-3,3a,5a,6,7,8,8a,8b-octahydro-as-indacene-3-acetic acid κ-lactone
204381-45-3

(3S,3aR,5aS,7S,8aR,8bS)-2-[(2R,3S,7S)-3-(tert-butyldiphenylsiloxy)-7-hydroxy-2-methylnonanoyl]-7-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-3,3a,5a,6,7,8,8a,8b-octahydro-as-indacene-3-acetic acid κ-lactone

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / 49percent aq. HF / acetonitrile / 24 h
2: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester
204381-41-9

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-7-[(2R,3S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,8a,8b-octahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
2: Jones reagent / acetone / 1.5 h / 0 °C
3: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
4: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
5: 63 percent / methanolic K2CO3 / 48 h / Heating
6: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
7: 91 percent / 49percent aq. HF / acetonitrile / 24 h
8: AgOTf3 / CH2Cl2 / 3 h
View Scheme
2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester
204381-17-9

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-[2-(4-methoxy-benzyloxy)-ethyl]-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

spinosyn A
131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
2: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
3: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
4: Jones reagent / acetone / 1.5 h / 0 °C
5: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
6: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
7: 63 percent / methanolic K2CO3 / 48 h / Heating
8: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
9: 91 percent / 49percent aq. HF / acetonitrile / 24 h
10: AgOTf3 / CH2Cl2 / 3 h
View Scheme
C25H31IO3Si

C25H31IO3Si

A

spinosyn A
131929-60-7

spinosyn A

B

C41H65NO10

C41H65NO10

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: Tetrabutylammoniumsalz der Diphenylphosphinsaeure; copper(I) thiophene-2-carboxylate; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere; Schlenk technique
2.1: tributylphosphine / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
4.1: manganese(IV) oxide / dichloromethane / 5 h / 20 °C
5.1: (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; trifluoroacetic acid / water; acetonitrile / 72 h / -20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C
6.2: 2 h / -78 °C
6.3: 20 h / -78 - 20 °C
7.1: silver(I) triflimide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); N-iodo-succinimide / acetone; water / 5 h / -15 - 20 °C
8.1: palladium diacetate; tetraethylammonium chloride; trifuran-2-yl-phosphane / toluene / 6 h / 90 °C / 2280.15 Torr / Molecular sieve
9.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C
10.1: dichloromethane / 1 h / 20 °C / Molecular sieve
10.2: 24 h / -30 °C
11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 0 °C / pH 7
12.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); silver trifluoromethanesulfonate / chlorobenzene / 25 h / 20 - 50 °C / Molecular sieve
View Scheme
C29H38O4Si

C29H38O4Si

A

spinosyn A
131929-60-7

spinosyn A

B

C41H65NO10

C41H65NO10

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: tributylphosphine / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
3.1: manganese(IV) oxide / dichloromethane / 5 h / 20 °C
4.1: (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; trifluoroacetic acid / water; acetonitrile / 72 h / -20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C
5.2: 2 h / -78 °C
5.3: 20 h / -78 - 20 °C
6.1: silver(I) triflimide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); N-iodo-succinimide / acetone; water / 5 h / -15 - 20 °C
7.1: palladium diacetate; tetraethylammonium chloride; trifuran-2-yl-phosphane / toluene / 6 h / 90 °C / 2280.15 Torr / Molecular sieve
8.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C
9.1: dichloromethane / 1 h / 20 °C / Molecular sieve
9.2: 24 h / -30 °C
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 5 h / 0 °C / pH 7
11.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); silver trifluoromethanesulfonate / chlorobenzene / 25 h / 20 - 50 °C / Molecular sieve
View Scheme
spinosyn A
131929-60-7

spinosyn A

C41H66BrNO11

C41H66BrNO11

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid; water In dimethyl sulfoxide at 0℃; for 0.5h;97.1%
spinosyn A
131929-60-7

spinosyn A

5,6-dihydrospinosyn A
187170-37-2

5,6-dihydrospinosyn A

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 48h;93%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 48h;93%
spinosyn A
131929-60-7

spinosyn A

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione
131929-68-5

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione

Conditions
ConditionsYield
With sulfuric acid In water at 80 - 90℃; for 24h;90%
With sulfuric acid In water at 80℃; for 2h; Hydrolysis;89%
With sulfuric acid89%
With sulfuric acid In dichloromethane at 80℃;
With sulfuric acid at 80℃;
spinosyn A
131929-60-7

spinosyn A

A

D-forosamine
56587-30-5

D-forosamine

B

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione
131929-68-5

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione

Conditions
ConditionsYield
With sulfuric acid; water at 80℃; for 2h;A n/a
B 89%
spinosyn A
131929-60-7

spinosyn A

(5R,6R)-5-hydroxy-6-bromospinosyn A

(5R,6R)-5-hydroxy-6-bromospinosyn A

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfuric acid In water; dimethyl sulfoxide at 0℃; for 0.166667h;86%
spinosyn A
131929-60-7

spinosyn A

N-demethyl-spinosyn A
131929-61-8

N-demethyl-spinosyn A

Conditions
ConditionsYield
With iodine; sodium acetate In methanol; water for 12h; Reflux;81%
With iodine; sodium acetate In methanol; water for 12h; Reflux;81%
spinosyn A
131929-60-7

spinosyn A

C41H65NO11

C41H65NO11

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3h;78%
spinosyn A
131929-60-7

spinosyn A

(1aR,1bR,3S,4aS,4bR,7R,8S,12S,15aS,15bR,15cS)-8-(((2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12-ethyl-7-methyl-3-(((2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,3,4,4a,7,8,9,10,11,12,15,15a,15b,15c-tetradecahydra-1aH-oxireno[2’,3':4,5]-as-indaceno[3,2-d][1] oxacyclododecine-6,14(1bH,4bH)-dione

(1aR,1bR,3S,4aS,4bR,7R,8S,12S,15aS,15bR,15cS)-8-(((2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12-ethyl-7-methyl-3-(((2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,3,4,4a,7,8,9,10,11,12,15,15a,15b,15c-tetradecahydra-1aH-oxireno[2’,3':4,5]-as-indaceno[3,2-d][1] oxacyclododecine-6,14(1bH,4bH)-dione

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2.5h;76%
spinosyn A
131929-60-7

spinosyn A

4''-ketospinosyn A
187168-48-5

4''-ketospinosyn A

Conditions
ConditionsYield
With pyridine; 1-chloromethyl-4-fluorotriethylenediamine tetrafluoroborate In acetonitrile at 0℃; for 1h;63%
spinosyn A
131929-60-7

spinosyn A

13,14-dihydrospinosyn A

13,14-dihydrospinosyn A

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 1h;57%
spinosyn A
131929-60-7

spinosyn A

(5S)-5,6-dihydro-5-hydroxyspinosyn A

(5S)-5,6-dihydro-5-hydroxyspinosyn A

Conditions
ConditionsYield
Stage #1: spinosyn A With mercury(II) trifluoroacetate In tetrahydrofuran; water at 23℃; for 0.5h;
Stage #2: With sodium hydroxide; sodium tetrahydroborate Further stages.;
30.4%
spinosyn A
131929-60-7

spinosyn A

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-2,13-dihydroxy-14-methyl-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione
149560-97-4

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-2,13-dihydroxy-14-methyl-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione

Conditions
ConditionsYield
With sulfuric acid In ethanol for 4.5h; Heating; Yield given;
Multi-step reaction with 2 steps
1: 89 percent / 1 N H2SO4 / H2O / 2 h / 80 °C
2: 66 percent / H2SO4 / methanol / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: water; sulfuric acid / 2 h / 80 °C
2: water; sulfuric acid / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid
2: sulfuric acid / methanol / Reflux
View Scheme
spinosyn A
131929-60-7

spinosyn A

A

(1aR,1bR,3S,4aS,4bR,7R,8S,12S,15aS,15bR,15cS)-8-(((2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12-ethyl-7-methyl-3-(((2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,3,4,4a,7,8,9,10,11,12,15,15a,15b,15c-tetradecahydra-1aH-oxireno[2’,3':4,5]-as-indaceno[3,2-d][1] oxacyclododecine-6,14(1bH,4bH)-dione

(1aR,1bR,3S,4aS,4bR,7R,8S,12S,15aS,15bR,15cS)-8-(((2R,5S,6R)-5-(dimethylamino)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12-ethyl-7-methyl-3-(((2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,3,4,4a,7,8,9,10,11,12,15,15a,15b,15c-tetradecahydra-1aH-oxireno[2’,3':4,5]-as-indaceno[3,2-d][1] oxacyclododecine-6,14(1bH,4bH)-dione

B

C41H65NO11

C41H65NO11

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 23℃;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 6h;A 120 mg
B 20 mg
spinosyn A
131929-60-7

spinosyn A

(4''S)-4''-desdimethylamino-4''-hydroxyspinosyn A
187168-79-2

(4''S)-4''-desdimethylamino-4''-hydroxyspinosyn A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 63 percent / pyridine; 1-chloromethyl-4-fluorotriethylenediamine tetrafluoroborate / acetonitrile / 1 h / 0 °C
2: 99 percent / Li(t-BuO)3AlH / diethyl ether; dioxane / 0.17 h / 0 °C
View Scheme
spinosyn A
131929-60-7

spinosyn A

C40H63NO10

C40H63NO10

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / aq. H2SO4 / H2O / 24 h / 80 - 90 °C
2: 36 percent / PPTS; BF3*OEt2 / 1,2-dichloro-ethane
3: 42 percent / aq. NH4OAc; Zn / tetrahydrofuran; methanol / 3.5 h / 20 °C
View Scheme
spinosyn A
131929-60-7

spinosyn A

C39H61NO10
849420-55-9

C39H61NO10

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 63 percent / pyridine; 1-chloromethyl-4-fluorotriethylenediamine tetrafluoroborate / acetonitrile / 1 h / 0 °C
2: 99 percent / Li(t-BuO)3AlH / diethyl ether; dioxane / 0.17 h / 0 °C
3: 91 percent / pyridine; DIPEA / CH2Cl2 / 1 h / 0 °C
4: 39 percent / NaN3 / dimethylformamide / 1 h / 120 °C
5: SnCl2*2H2O / methanol / 20 h / 20 °C
View Scheme
spinosyn A
131929-60-7

spinosyn A

(4''R)-4''-desdimethylamino-4''-(azido)spinosyn A
849420-54-8

(4''R)-4''-desdimethylamino-4''-(azido)spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 63 percent / pyridine; 1-chloromethyl-4-fluorotriethylenediamine tetrafluoroborate / acetonitrile / 1 h / 0 °C
2: 99 percent / Li(t-BuO)3AlH / diethyl ether; dioxane / 0.17 h / 0 °C
3: 91 percent / pyridine; DIPEA / CH2Cl2 / 1 h / 0 °C
4: 39 percent / NaN3 / dimethylformamide / 1 h / 120 °C
View Scheme
spinosyn A
131929-60-7

spinosyn A

4''-epispinosyn A

4''-epispinosyn A

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 63 percent / pyridine; 1-chloromethyl-4-fluorotriethylenediamine tetrafluoroborate / acetonitrile / 1 h / 0 °C
2: 99 percent / Li(t-BuO)3AlH / diethyl ether; dioxane / 0.17 h / 0 °C
3: 91 percent / pyridine; DIPEA / CH2Cl2 / 1 h / 0 °C
4: 39 percent / NaN3 / dimethylformamide / 1 h / 120 °C
5: SnCl2*2H2O / methanol / 20 h / 20 °C
6: 7.0 mg / acetonitrile / 2 h / Heating
View Scheme
spinosyn A
131929-60-7

spinosyn A

(4''S)-4''-desdimethylamino-4''-(methanesulfonyloxy)spinosyn A
849420-51-5

(4''S)-4''-desdimethylamino-4''-(methanesulfonyloxy)spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 63 percent / pyridine; 1-chloromethyl-4-fluorotriethylenediamine tetrafluoroborate / acetonitrile / 1 h / 0 °C
2: 99 percent / Li(t-BuO)3AlH / diethyl ether; dioxane / 0.17 h / 0 °C
3: 91 percent / pyridine; DIPEA / CH2Cl2 / 1 h / 0 °C
View Scheme
spinosyn A
131929-60-7

spinosyn A

C43H64Cl3NO12

C43H64Cl3NO12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / aq. H2SO4 / H2O / 24 h / 80 - 90 °C
2: 36 percent / PPTS; BF3*OEt2 / 1,2-dichloro-ethane
View Scheme
spinosyn A
131929-60-7

spinosyn A

C41H65NO11

C41H65NO11

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / conc. H2SO4; NBS / dimethylsulfoxide; H2O / 0.17 h / 0 °C
2: 96 percent / NaH / tetrahydrofuran / 0.5 h
View Scheme

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