(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Base Information

Chemical Name:(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene
CAS No.:116700-82-4
Molecular Formula:C₃₁H₆₂O₄Si₃
Molecular Weight:583.087
Hs Code.:

(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Synonyms:(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

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Chemical Property of (3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

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Technology Process of (3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

There total 14 articles about (3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene 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: 86.0%

: 13170-43-9
(trimethylsilyl)methylmagnesium chloride

: 116724-52-8
(3SR,4RS)-1-<(diethoxyphosphoryl)oxy>-2-(methoxycarbonyl)-4-(1-methylethyl)-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

: 116700-82-4
(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Guidance literature:: With bis(acetylacetonate)nickel(II); In tetrahydrofuran; diethyl ether; for 11h; Ambient temperature;
DOI:10.1021/ja00232a027

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 116700-82-4
(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 9 h / Ambient temperature

2: 35.4 g / diisobutylaluminum hydride / hexane; tetrahydrofuran / 1.) -78 deg C, 2 h; 2.) 30 min, 0 deg C

3: 86 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / Ambient temperature

4: 74 percent / bromine / CH₂Cl₂ / 0.17 h / -78 °C

5: 92 percent / DBU / benzene / 7.5 h / Heating

6: tert-butyllithium / pentane; diethyl ether / 0.33 h / -78 °C

7: 1.) 2-thienylcyanocopperlithium / 1.) THF, pentane, ether, -78 deg C, 1 h; 2.) 3 h, -78 deg C

8: 1.) NaH / 1.) room t., 20 min, THF; 2.) 0 deg C, 2 h

9: 86 percent / Ni(acac)2 / tetrahydrofuran; diethyl ether / 11 h / Ambient temperature

With bis(acetylacetonate)nickel(II); bromine; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; dmap; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; benzene;
DOI:10.1021/ja00232a027

Reference yield:

: 116700-73-3
2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol

: 116700-82-4
(3SR,4RS)-2-(methoxycarbonyl)-4-(1-methylethyl)-1-<(trimethylsilyl)methyl>-3-<3-(tert-butyldimethylsiloxy)-2-<(tert-butyldimethylsiloxy)methyl>prop-1-en-1-yl>cyclohex-1-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / Ambient temperature

2: 74 percent / bromine / CH₂Cl₂ / 0.17 h / -78 °C

3: 92 percent / DBU / benzene / 7.5 h / Heating

4: tert-butyllithium / pentane; diethyl ether / 0.33 h / -78 °C

5: 1.) 2-thienylcyanocopperlithium / 1.) THF, pentane, ether, -78 deg C, 1 h; 2.) 3 h, -78 deg C

6: 1.) NaH / 1.) room t., 20 min, THF; 2.) 0 deg C, 2 h

7: 86 percent / Ni(acac)2 / tetrahydrofuran; diethyl ether / 11 h / Ambient temperature

With bis(acetylacetonate)nickel(II); bromine; tert.-butyl lithium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; dmap; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; benzene;
DOI:10.1021/ja00232a027