(1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

Base Information

Chemical Name:(1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one
CAS No.:382654-95-7
Molecular Formula:C₂₈H₃₄O₄Si
Molecular Weight:462.661
Hs Code.:

Synonyms:(1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

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Chemical Property of (1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

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Technology Process of (1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

There total 11 articles about (1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one 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: 92.0%

: 382654-94-6
C₃₅H₄₈O₅Si

: 382654-95-7
(1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja0169769

Reference yield: 92.0%

: 382655-00-7
C₃₃H₄₄O₅Si

: 382654-95-7
(1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja0169769

Reference yield:

: 382654-90-2
2-bromo-3-(tert-butyl-diphenyl-silanyloxymethyl)-4,4-dimethoxy-cyclohexa-2,5-dienone

: 382654-95-7
(1S,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-((E)-pent-1-enyl)-7-oxa-bicyclo[4.1.0]hept-3-en-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / pyridinium p-toluenesulfonate / benzene / 4 h / 70 °C

2: 85 percent / Ph₃COOH; KHMDS / tetrahydrofuran; toluene / 6.5 h / -78 - -10 °C

3: 73 percent / Pd₂dba3*CHCl₃ / CH₂Cl₂ / 25 h / 35 °C

4: 85 percent / DIBAL-H / tetrahydrofuran; hexane / 0.25 h / -78 °C

5: 92 percent / aq. HF / acetonitrile / 0.08 h / 0 °C

With trityl hydroperoxide; hydrogen fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1021/ja0169769