1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol

Base Information

• Chemical Name: 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol
• CAS No.: 212690-10-3
• Molecular Formula: C₄₀H₇₂O₈Si₂
• Molecular Weight: 737.178

Synonyms:1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol

Chemical Property of 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol

Chemical Property:

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Technology Process of 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol

There total 7 articles about 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-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: 88.0%

1-{[(4-iodobutyl)oxy]methyl}-4-methoxybenzene (164933-38-4) + [(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-acetaldehyde (212689-81-1) → 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol (212690-10-3)

Guidance literature:

With tert.-butyl lithium; In diethyl ether; at -78 ℃;

DOI:10.1021/ja981257o

Reference yield:

(8S,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-tetradec-13-ene-4,7-dione → 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol (212690-10-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / camphorsulfonic acid, MeOH

2: 95 percent / 2,6-lutidine

3: OsO₄, NMO

4: NaIO₄

5: 88 percent / t-BuLi / diethyl ether / -78 °C

With 2,6-dimethylpyridine; methanol; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tert.-butyl lithium; In diethyl ether;

DOI:10.1021/ja981257o

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 1-[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-6-(4-methoxy-benzyloxy)-hexan-2-ol (212690-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 2,6-lutidine

2: OsO₄, NMO

3: NaIO₄

4: 88 percent / t-BuLi / diethyl ether / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tert.-butyl lithium; In diethyl ether;

DOI:10.1021/ja981257o

upstream raw materials:

1-{[(4-iodobutyl)oxy]methyl}-4-methoxybenzene

[(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-yl]-acetaldehyde

t-butyldimethylsiyl triflate

(2R,5S,6S,8S,10S)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane

Downstream raw materials:

C₅₆H₉₈O₁₀S₂Si₂

(2R,5S,6S,8S,10S)-5-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane

tert-Butyl-{(2R,5S,6S,8S,10S)-10-[1,3]dithian-2-ylmethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-dimethyl-silane

tert-Butyl-{(2R,5S,6S,8S,10S)-10-iodomethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-dimethyl-silane

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