(5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

Base Information

Chemical Name:(5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol
CAS No.:1207434-20-5
Molecular Formula:C₄₂H₇₀O₄Si₃
Molecular Weight:723.272
Hs Code.:

Synonyms:(5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

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Chemical Property of (5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

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Technology Process of (5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

There total 14 articles about (5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-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: 99.0%

: 1207434-19-2
(5S,6R,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-one

: 1207434-20-5
(5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at -78 - 15 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo301066p

Reference yield: 96.0%

: 1207434-19-2
(5S,6R,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-one

: 1207434-38-5
(5S,6S,7R,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

: 1207434-20-5
(5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

Guidance literature:: (5S,6R,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-one; With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In ethanol; at -78 - -15 ℃; for 5h;

With potassium carbonate; In ethanol; at 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol902829e

Reference yield:

: 958635-16-0
(R)-6-[(tert-butyldiphenylsilyl)oxy]-1,2-epoxyhexane

: 1207434-20-5
(5S,6S,7S,11R)-11-(tert-butyldimethylsilyloxy)-2,2,3,3,6,18,18-heptamethyl-17,17-diphenyl-5-vinyl-4,16-dioxa-3,17-disilanonadec-8-yn-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 0.5 h / -78 °C

2.1: potassium carbonate / methanol / 16 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C

4.2: -78 - 20 °C

5.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / ethanol / 5 h / -78 - -15 °C

5.2: 20 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride heptahydrate; potassium carbonate; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; 5.1: Luche reduction;
DOI:10.1021/ol902829e