[(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester
• CAS No.: 866430-81-1
• Molecular Formula: C₂₀H₃₆O₄Si
• Molecular Weight: 368.589
• Mol file: 866430-81-1.mol

Synonyms:[(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Chemical Property of [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

There total 4 articles about [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl 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:

[(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester (866430-79-7) → [(1R,2R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester (866430-80-0) + [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester (866430-81-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -50 ℃;

DOI:10.1016/j.tetlet.2005.07.152

Reference yield:

5-but-3-enyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone → [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester (866430-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / LDA / -78 °C

2: NaBH₄; CeCl₃ / methanol / -50 °C

With sodium tetrahydroborate; cerium(III) chloride; lithium diisopropyl amide; In methanol; 2: Luche reduction;

DOI:10.1016/j.tetlet.2005.07.152

Reference yield:

(1S,4R,4aS,8S,8aR)-7-But-3-enyl-8-(tert-butyl-dimethyl-silanyloxy)-4,4a,6,7,8,8a-hexahydro-1H-1,4-methano-naphthalen-5-one → [(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester (866430-81-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / diphenyl ether / 0.17 h / 220 °C

2: 60 percent / LDA / -78 °C

3: NaBH₄; CeCl₃ / methanol / -50 °C

With sodium tetrahydroborate; cerium(III) chloride; lithium diisopropyl amide; In methanol; diphenylether; 1: retro-Diels-Alder reaction / 3: Luche reduction;

DOI:10.1016/j.tetlet.2005.07.152

upstream raw materials:

[(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester

(1S,4R,4aS,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

Downstream raw materials:

[6-but-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-cyclohex-3-enyl]-acetic acid ethyl ester

(1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one

[6-but-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-cyclohex-3-enyl]-acetic acid 1-methyl-allyl ester

(Z)-(1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,11,12,12a-octahydro-7-oxa-benzocyclodecen-6-one