(E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one

Base Information

• Chemical Name: (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one
• CAS No.: 141619-10-5
• Molecular Formula: C₄₅H₈₁IO₈Si₃
• Molecular Weight: 961.294

Synonyms:

Chemical Property of (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one

There total 5 articles about (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-((2R,3R,3aS,5R,6R,7aS)-6-Benzyloxy-2-methoxy-3-methyl-hexahydro-furo[3,2-b]pyran-5-yl)-ethanol (141619-05-8) → (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one (141619-10-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Dess-Martin reagent, 2) KN(TMS)2, 18-crown-6 / 2) THF, -78 deg C

2: DIBAL / pentane; CH₂Cl₂ / -78 °C

3: 1) t-BuOOH, diethyl L-(+)-tartrate, Ti(i-PrO)4, 2) p-TsOH, H₂O / 1) CH₂Cl₂, -20 deg C, 2) CHCl₃, rt

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; In dichloromethane; pentane;

DOI:10.1016/S0040-4039(00)91673-3

Reference yield:

(Z)-4-((2R,3R,3aS,5R,6R,7aS)-6-Benzyloxy-2-methoxy-3-methyl-hexahydro-furo[3,2-b]pyran-5-yl)-but-2-enoic acid methyl ester → (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one (141619-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL / pentane; CH₂Cl₂ / -78 °C

2: 1) t-BuOOH, diethyl L-(+)-tartrate, Ti(i-PrO)4, 2) p-TsOH, H₂O / 1) CH₂Cl₂, -20 deg C, 2) CHCl₃, rt

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; water; diisobutylaluminium hydride; toluene-4-sulfonic acid; In dichloromethane; pentane;

DOI:10.1016/S0040-4039(00)91673-3

Reference yield:

(3R,3aS,5R,6R,7aS)-6-Benzyloxy-5-hydroxymethyl-3-methyl-hexahydro-furo[3,2-b]pyran-2-one (141619-04-7) → (E)-(2S,6S,7S)-2-[(2S,3aR,5S,6S,7aR)-2-[(S)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-5-yl]-9-iodo-7-(4-methoxy-benzyloxy)-6-methyl-non-8-en-4-one (141619-10-5)

Guidance literature:

Multi-step reaction with 5 steps

2: 1) Dess-Martin reagent, 2) KN(TMS)2, 18-crown-6 / 2) THF, -78 deg C

3: DIBAL / pentane; CH₂Cl₂ / -78 °C

4: 1) t-BuOOH, diethyl L-(+)-tartrate, Ti(i-PrO)4, 2) p-TsOH, H₂O / 1) CH₂Cl₂, -20 deg C, 2) CHCl₃, rt

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; In dichloromethane; pentane;

DOI:10.1016/S0040-4039(00)91673-3

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-1-((2S,3aR,4aS,5R,6R,7aS,8aR)-6-Methoxy-5-methyl-octahydro-difuro[3,2-b;2',3'-e]pyran-2-yl)-ethane-1,2-diol

[(3S,4R)-5-Bromo-3-(4-methoxy-benzyloxy)-4-methyl-pent-1-ynyl]-trimethyl-silane

2-((2R,3R,3aS,5R,6R,7aS)-6-Benzyloxy-2-methoxy-3-methyl-hexahydro-furo[3,2-b]pyran-5-yl)-ethanol

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