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

Base Information

• Chemical Name: (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane
• CAS No.: 905312-33-6
• Molecular Formula: C₂₈H₄₄O₇Si
• Molecular Weight: 520.739
• Mol file: 905312-33-6.mol

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

Chemical Property of (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane

There total 7 articles about (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane 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:

Acetic acid (1S,2R,3R,4R,6S)-2-[(1S,2S)-1-acetoxy-2-(4-methoxy-benzyloxy)-propyl]-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester → (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane (905312-33-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

Acetic acid (1S,2S,3R,4R,6S)-2-((1S,2S)-1-acetoxy-2-triethylsilanyloxy-propyl)-6-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-vinyl-cyclohexyl ester → (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane (905312-33-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone (581060-33-5) → (1S,2S,3R,4R,5R)-2-acetoxy-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-acetoxy-2'-hydroxypropyl]-4-vinylcyclohexane (905312-33-6)

Guidance literature:

Multi-step reaction with 4 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

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

upstream raw materials:

(1S,2S,3R,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-4-vinylcyclohexan-2-ol

(1S,2S,3R,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

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

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

Downstream raw materials:

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