(1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

Base Information

Chemical Name:(1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one
CAS No.:1289117-08-3
Molecular Formula:C₁₉H₂₈O₃SSi
Molecular Weight:364.581
Hs Code.:

Synonyms:(1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

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Technology Process of (1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

There total 3 articles about (1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-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: 94.0%

: 1289117-43-6
C₁₃H₁₄O₃S

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1289117-08-3
(1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere; Reflux;
DOI:10.1002/ejoc.201001527

Reference yield:

: (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-methyl-6-phenylthiocyclohex-2-enone

: 1289117-07-2
(+)-(1R,3S,5S,6S)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

: 1289117-08-3
(1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: With dihydrogen peroxide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; optical yield given as %de;
DOI:10.1002/ejoc.201001527

Reference yield:

: 5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

: 1289117-08-3
(1S,3S,5S,6R)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C

2: 1H-imidazole / dichloromethane / 16 h / 0 °C / Inert atmosphere; Reflux

With 1H-imidazole; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201001527