(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

Base Information

Chemical Name:(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one
CAS No.:187862-70-0
Molecular Formula:C₄₂H₆₄O₄Si₂
Molecular Weight:689.139
Hs Code.:

Synonyms:(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

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Chemical Property of (4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

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Technology Process of (4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

There total 21 articles about (4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-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: 75.0%

: 187862-65-3
C₄₃H₆₆O₃Si₂

: 187862-70-0
(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

Guidance literature:: C₄₃H₆₆O₃Si₂; With osmium(VIII) oxide; trimethylamine-N-oxide; water; In tetrahydrofuran; toluene; tert-butyl alcohol;

With lead(IV) acetate; In diethyl ether; for 0.25h; Further stages.;
DOI:10.1021/jo001767c

Reference yield:

: 187862-52-8
(E)-(5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undec-3-enoic acid methyl ester

: 187862-70-0
(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: O₃ / pyridine / methanol / -78 °C

1.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

2.1: 71 percent / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

3.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

4.1: OsO₄; Me₃NO; water / 2-methyl-propan-2-ol; tetrahydrofuran; toluene

4.2: 75 percent / Pb(OAc)4 / diethyl ether / 0.25 h

With 2,6-dimethylpyridine; osmium(VIII) oxide; trimethylamine-N-oxide; water; titanium tetrachloride; ozone; pyridine; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo001767c

Reference yield:

: 187862-43-7
(R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-hexanal

: 187862-70-0
(4S,5R,6S,9R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undecan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

2.1: O₃ / pyridine / methanol / -78 °C

2.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

3.1: 71 percent / TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

5.1: OsO₄; Me₃NO; water / 2-methyl-propan-2-ol; tetrahydrofuran; toluene

5.2: 75 percent / Pb(OAc)4 / diethyl ether / 0.25 h

With 2,6-dimethylpyridine; osmium(VIII) oxide; trimethylamine-N-oxide; trimethylsilyl trifluoromethanesulfonate; water; titanium tetrachloride; ozone; pyridine; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo001767c