(1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol

Base Information

• Chemical Name: (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol
• CAS No.: 218785-08-1
• Molecular Formula: C₄₇H₇₄O₉Si
• Molecular Weight: 811.185

Synonyms:(1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol

Chemical Property of (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol

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Technology Process of (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol

There total 24 articles about (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol 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: 83.0%

(4S,5S)-4-((S)-2-Bromo-1-methyl-allyl)-2,2,5-trimethyl-[1,3]dioxane (218785-16-1) + [(2R,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]dec-9-yloxy]-tert-butyl-dimethyl-silane (218785-05-8) → (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol (218785-08-1)

Guidance literature:

With (Th)Cu(CN)Li; tert.-butyl lithium;

DOI:10.1021/jo981813x

Reference yield:

Trifluoro-methanesulfonic acid (S)-1-methylene-2-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propyl ester (218785-25-2) → (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol (218785-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (Bu₃Sn)2; n-BuLi; lithium 2-thienylcyanocuprate

1.2: NBS

2.1: t-BuLi / diethyl ether / 0.5 h / -78 - 0 °C

2.2: lithium 2-thienylcyanocuprate / 0.5 h / -78 - -45 °C

2.3: 83 percent / 48 h / -5 °C

With n-butyllithium; tert.-butyl lithium; bis(tri-n-butyltin); thien-2-yl(cyano)copper lithium; In diethyl ether; 1.1: Substitution / 1.2: Substitution / 2.1: Metallation / 2.2: Addition / 2.3: coupling;

DOI:10.1021/ja992134m

Reference yield:

(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol (162991-28-8) → (1R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-1-ol (218785-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / Et₃N

2.1: t-BuLi / diethyl ether / 0.5 h / -78 - 0 °C

2.2: lithium 2-thienylcyanocuprate / 0.5 h / -78 - -45 °C

2.3: 83 percent / 48 h / -5 °C

With tert.-butyl lithium; triethylamine; In diethyl ether; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 2.3: coupling;

DOI:10.1021/ja992134m

upstream raw materials:

(4S,5S)-4-((S)-2-Bromo-1-methyl-allyl)-2,2,5-trimethyl-[1,3]dioxane

[(2R,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]dec-9-yloxy]-tert-butyl-dimethyl-silane

(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

2-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol

Downstream raw materials:

(2S,3S,4R,5R,7R)-7-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-7-methoxy-2,4-dimethyl-heptane-1,3,5-triol

C₆₁H₁₀₈O₁₁Si₃

C₆₃H₁₂₅O₁₃PSi₅

(1R,3R,4R)-1-[(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentan-3-ol

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