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

Base Information

Chemical Name:(3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one
CAS No.:493034-00-7
Molecular Formula:C₂₅H₃₈O₅Si
Molecular Weight:446.659
Hs Code.:

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

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

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

There total 1 articles about (3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-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:

: Benzoic acid (1R,2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-prop-2-ynyl)-2,4-dimethyl-5-triethylsilanyloxy-hexyl ester

: 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

Guidance literature:: Benzoic acid (1R,2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-prop-2-ynyl)-2,4-dimethyl-5-triethylsilanyloxy-hexyl ester; With trifluoroacetic acid; In tetrahydrofuran; water; at 23 ℃; for 1.33333h;

With pyridine; Dess-Martin periodane; In diethyl ether; dichloromethane; at 23 ℃; Further stages.;
DOI:10.1021/ol027257h

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:

: 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

: 749900-27-4
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: 45 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

2.1: 84 percent / tin(II) chloride; silver perchlorate / diethyl ether / 0.5 h / -15 °C

3.1: 90 percent / tributyltin hydride; triethylborane / toluene; various solvent(s) / 12 h / 23 °C

With triethyl borane; tri-n-butyl-tin hydride; silver perchlorate; triethylamine; tin(ll) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/ol027257h