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

Base Information

• Chemical Name: (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol
• CAS No.: 905312-31-4
• Molecular Formula: C₃₉H₅₄O₈SSi
• Molecular Weight: 711.004
• Mol file: 905312-31-4.mol

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

Chemical Property of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol

There total 13 articles about (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-4-vinylcyclohexan-2-ol (581060-38-0) → (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol (905312-31-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one (581060-36-8) → (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol (905312-31-4)

Guidance literature:

Multi-step reaction with 4 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: 85 percent / diethyl ether / 0.33 h / -78 °C

3.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

4.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

With n-butyllithium; copper(l) cyanide; acetic acid; methanesulfonyl chloride; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

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,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol (905312-31-4)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 85 percent / diethyl ether / 0.33 h / -78 °C

2.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

3.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

With n-butyllithium; copper(l) cyanide; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1016/j.tet.2006.04.079

upstream raw materials:

p-toluenesulfonyl chloride

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

(+)-(2R)-methyl 2-(p-methoxybenzyloxy)propanoate

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-mrthoxymethyloxy-cyclohexancarboxylic acid

(4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid

(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

(3S,4S,5S,6S,10S)-4-azido-6-benzyloxy-5,8-dihydroxy-3-methyl-5,6,7,4a-tetrahydroisochroman-1-one