(1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

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Chemical Name:(1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol
CAS No.:512783-01-6
Molecular Formula:C₃₂H₅₀O₄Si
Molecular Weight:526.832
Hs Code.:

Synonyms:(1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

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Chemical Property of (1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

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Technology Process of (1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

There total 5 articles about (1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-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: 96.0%

: 200704-86-5
(1S,3R,4S)-3-(4-Methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-one

: 512783-00-5
tert-butyl-(6-iodo-4-methylene-hex-5-enyloxy)-dimethyl-silane

: 512783-01-6
(1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: tert-butyl-(6-iodo-4-methylene-hex-5-enyloxy)-dimethyl-silane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.0333333h;

(1S,3R,4S)-3-(4-Methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-one; In diethyl ether; pentane; at -78 - 0 ℃; for 3.5h;
DOI:10.1021/jo020627v

Reference yield:

: 64180-78-5
4-bromopent-4-en-1-ol

: 512783-01-6
(1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 15.74 g / Et₃N; DBU / CH₂Cl₂

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C

3.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

3.2: 88 percent / tetrahydrofuran / -78 - -30 °C

4.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C

4.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C

With tert.-butyl lithium; sodium hexamethyldisilazane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 3.2: Wittig condensation;
DOI:10.1021/jo020627v

Reference yield:

: 120001-35-6
((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane

: 512783-01-6
(1S,2S,3R,4S)-2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methylene-hex-1-enyl]-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

1.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C

2.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

2.2: 88 percent / tetrahydrofuran / -78 - -30 °C

3.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C

3.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C

With tert.-butyl lithium; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; pentane; 2.2: Wittig condensation;
DOI:10.1021/jo020627v