(1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

Base Information

Chemical Name:(1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol
CAS No.:1375467-50-7
Molecular Formula:C₂₂H₂₈O₃Si
Molecular Weight:368.548
Hs Code.:

Synonyms:(1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

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Chemical Property of (1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

Chemical Property:

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Technology Process of (1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

There total 8 articles about (1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-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:

: 1375467-48-3
(1R,5R)-5-(tert-butyldiphenylsilyloxymethyl)cyclopent-2-enol

: 1375467-50-7
(1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

: 1375467-51-8
(1R,2S,3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 19h; diastereoselective reaction;
DOI:10.1016/j.tetasy.2012.03.001

Reference yield:

: 1375467-30-3
(R)-2-(tert-butyldiphenylsilanyloxymethyl)-pent-4-enal

: 1375467-50-7
(1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-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: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 19 h / 0 - 20 °C

With Grubbs catalyst first generation; sodium tetrahydroborate; oxalyl dichloride; cerium(III) chloride heptahydrate; sodium hydrogencarbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1016/j.tetasy.2012.03.001

Reference yield:

: 1375467-32-5
(R)-4-(tert-butyldiphenylsilanyloxymethyl)-hepta-1,6-dien-3-one

: 1375467-50-7
(1S,2S,3R,5R)-3-(tert-butyldiphenylsilyloxymethyl)-6-oxa-bicyclo[3.1.0]hexan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 19 h / 0 - 20 °C

With Grubbs catalyst first generation; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1016/j.tetasy.2012.03.001