(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Base Information

Chemical Name:(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one
CAS No.:493033-94-6
Molecular Formula:C₃₉H₇₀O₇Si₃
Molecular Weight:735.237
Hs Code.:

(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Synonyms:(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

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Chemical Property of (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

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Technology Process of (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

There total 8 articles about (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-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: 66.0%

: 140223-32-1
(2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde

: 749900-19-4
(3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)siloxy]-6-[(benzoyl)oxy]-7-methoxynon-8-yn-2-one

: 493033-94-6
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: (3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)siloxy]-6-[(benzoyl)oxy]-7-methoxynon-8-yn-2-one; With chloro-trimethyl-silane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ja048493l

Reference yield: 45.0%

: 493034-00-7
(3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one

: 75-77-4
chloro-trimethyl-silane

: 140223-32-1
(2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde

: 493033-94-6
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: (3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one; chloro-trimethyl-silane; With triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

(2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2h; Further stages.;
DOI:10.1021/ol027257h

Reference yield:

: 251301-00-5
(2R,3S)-3-[(-O-tert-Butyldimethylsilyl)oxy]-2-methylbutan-1-ol

: 493033-94-6
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 61 mg / pyridine; Dess-Martin periodinane; H₂O / CH₂Cl₂ / 23 °C

2.1: TMSCl; Et₃N; LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 66 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

With pyridine; chloro-trimethyl-silane; water; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.1: Dess-Martin oxidation / 2.2: Mukaiyama aldol coupling;
DOI:10.1021/ja048493l