Cyclohexanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-ethenyl-2-[(1S,2S)-1-hydroxy-2 -[(4-methoxyphenyl)methoxy]propyl]-6-(phenylmethoxy)-, (2R,3R,4R,6S)-

Base Information

• Chemical Name: Cyclohexanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-ethenyl-2-[(1S,2S)-1-hydroxy-2 -[(4-methoxyphenyl)methoxy]propyl]-6-(phenylmethoxy)-, (2R,3R,4R,6S)-
• CAS No.: 581060-37-9
• Molecular Formula: C32H46O6Si
• Molecular Weight: 554.799
• Mol file: 581060-37-9.mol

Synonyms:

Chemical Property of Cyclohexanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-ethenyl-2-[(1S,2S)-1-hydroxy-2 -[(4-methoxyphenyl)methoxy]propyl]-6-(phenylmethoxy)-, (2R,3R,4R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclohexanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-ethenyl-2-[(1S,2S)-1-hydroxy-2 -[(4-methoxyphenyl)methoxy]propyl]-6-(phenylmethoxy)-, (2R,3R,4R,6S)-

There total 10 articles about Cyclohexanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-ethenyl-2-[(1S,2S)-1-hydroxy-2 -[(4-methoxyphenyl)methoxy]propyl]-6-(phenylmethoxy)-, (2R,3R,4R,6S)- 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: 72.0%

vinyllithium (917-57-7) + (S)-(p-methoxybenzyloxy)propanal (126361-27-1) + (4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone (581060-33-5) → (2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-3-vinylcyclohexan-1-one (581060-37-9)

Guidance literature:

vinyllithium; (4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone; With CuCN; In diethyl ether; at -78 ℃; for 0.25h;

(S)-(p-methoxybenzyloxy)propanal; In diethyl ether; at -78 ℃; for 1.5h;

DOI:10.1016/S0040-4039(03)01186-9

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-3-vinylcyclohexan-1-one (581060-37-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CSA / CH₂Cl₂ / 15 h / 20 °C

2.1: diisobutylaluminum hydride / CH₂Cl₂; toluene / 0.33 h / -78 °C

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

3.2: diethyl ether / 0.5 h / -78 °C

3.3: 72 percent / diethyl ether / 0.33 h / -78 °C

With camphor-10-sulfonic acid; copper(l) cyanide; diisobutylaluminium hydride; In diethyl ether; dichloromethane; toluene;

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) → (2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-3-vinylcyclohexan-1-one (581060-37-9)

Guidance literature:

Multi-step reaction with 2 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: 72 percent / diethyl ether / 0.33 h / -78 °C

With copper(l) cyanide; methanesulfonyl chloride; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2006.04.079

upstream raw materials:

vinyllithium

(S)-(p-methoxybenzyloxy)propanal

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

O-(4-methoxybenzyl)-trichloroacetimidate

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

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