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

Base Information

• Chemical Name: {(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane
• CAS No.: 218785-31-0
• Molecular Formula: C₄₈H₇₆O₉Si
• Molecular Weight: 825.212

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

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

Chemical Property:

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

There total 26 articles about {(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane 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: 96.0%

(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) + methyl iodide (74-88-4) → {(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane (218785-31-0)

Guidance literature:

With potassium hexamethylsilazane;

DOI:10.1021/jo981813x

Reference yield:

(4S,5S)-4-((S)-2-Bromo-1-methyl-allyl)-2,2,5-trimethyl-[1,3]dioxane (218785-16-1) → {(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane (218785-31-0)

Guidance literature:

Multi-step reaction with 2 steps

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

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

1.3: 83 percent / 48 h / -5 °C

2.1: 96 percent / KHMDS

With tert.-butyl lithium; potassium hexamethylsilazane; In diethyl ether; 1.1: Metallation / 1.2: Addition / 1.3: coupling / 2.1: Methylation;

DOI:10.1021/ja992134m

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) → {(2S,3S,5S,7R,8S,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-2-[(1R,4R)-1-methoxy-3-methylene-4-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-pentyl]-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yloxy}-tert-butyl-dimethyl-silane (218785-31-0)

Guidance literature:

Multi-step reaction with 3 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

3.1: 96 percent / KHMDS

With n-butyllithium; tert.-butyl lithium; bis(tri-n-butyltin); potassium hexamethylsilazane; thien-2-yl(cyano)copper lithium; In diethyl ether; 1.1: Substitution / 1.2: Substitution / 2.1: Metallation / 2.2: Addition / 2.3: coupling / 3.1: Methylation;

DOI:10.1021/ja992134m

upstream raw materials:

(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

methyl iodide

(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:

(1R,4S)-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-one

(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

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