Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

Base Information

Chemical Name:Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester
CAS No.:905312-51-8
Molecular Formula:C₂₉H₄₆O₉SSi
Molecular Weight:598.83
Hs Code.:

Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

Synonyms:Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

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Chemical Property of Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

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Technology Process of Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

There total 8 articles about Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester 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: 93.0%

: 905312-33-6
(1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane

: 124-63-0
methanesulfonyl chloride

: 905312-51-8
Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

Guidance literature:: With pyridine; dmap; at 0 - 20 ℃; for 1.5h;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 581060-33-5
(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

: 905312-51-8
Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 51 percent / diethyl ether / 2 h / -78 °C

2.1: 66 percent / NaBH₄ / methanol / 0.17 h / 0 °C

3.1: pyridine; DMAP / 12 h / 0 - 20 °C

4.1: 22.7 mg / DDQ / CH₂Cl₂; H₂O / 1 h / 0 - 20 °C

5.1: 93 percent / pyridine; DMAP / 1.5 h / 0 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; copper(l) cyanide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 581060-36-8
(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one

: 905312-51-8
Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-methanesulfonyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

1.2: 3.50 g / HCl / H₂O

2.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

2.2: diethyl ether / 0.5 h / -78 °C

2.3: 51 percent / diethyl ether / 2 h / -78 °C

3.1: 66 percent / NaBH₄ / methanol / 0.17 h / 0 °C

4.1: pyridine; DMAP / 12 h / 0 - 20 °C

5.1: 22.7 mg / DDQ / CH₂Cl₂; H₂O / 1 h / 0 - 20 °C

6.1: 93 percent / pyridine; DMAP / 1.5 h / 0 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; copper(l) cyanide; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tet.2006.04.079