(1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

Base Information

Chemical Name:(1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol
CAS No.:1375467-40-5
Molecular Formula:C₂₄H₃₂O₂Si
Molecular Weight:380.602
Hs Code.:

Synonyms:(1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

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Chemical Property of (1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

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Technology Process of (1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

There total 8 articles about (1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]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: 75.0%

: 74-95-3
1,1-dibromomethane

: (1R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-cyclohex-2-enol

: 1375467-40-5
(1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

Guidance literature:: With zinc/copper couple; iodine; In diethyl ether; for 0.5h; diastereoselective reaction; Reflux;
DOI:10.1016/j.tetasy.2012.03.001

Reference yield:

: 1375467-37-0
5-(tert-butyldiphenylsilanyloxymethyl)-octa-1,7-dien-3-ol

: 1375467-40-5
(1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

1.2: -78 - 20 °C

2.1: Grubbs catalyst first generation / dichloromethane / 20 °C

3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / 3 h / 0 - 20 °C

4.1: zinc/copper couple; iodine / diethyl ether / 0.5 h / Reflux

With Grubbs catalyst first generation; sodium tetrahydroborate; oxalyl dichloride; cerium(III) chloride heptahydrate; zinc/copper couple; iodine; dimethyl sulfoxide; In diethyl ether; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation;
DOI:10.1016/j.tetasy.2012.03.001

Reference yield:

: 1375467-36-9
(R)-3-(tert-butyldiphenylsilanyloxymethyl)-hex-5-enal

: 1375467-40-5
(1S,2R,4R,6R)-4-(tert-butyldiphenylsilyloxymethyl)bicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 2 h / -78 - 20 °C

1.2: Saturated solution

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

2.2: -78 - 20 °C

3.1: Grubbs catalyst first generation / dichloromethane / 20 °C

4.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / 3 h / 0 - 20 °C

5.1: zinc/copper couple; iodine / diethyl ether / 0.5 h / Reflux

With Grubbs catalyst first generation; sodium tetrahydroborate; oxalyl dichloride; cerium(III) chloride heptahydrate; zinc/copper couple; iodine; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1016/j.tetasy.2012.03.001