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

Base Information

Chemical Name:(+)-(1R,3R,5S,6S)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one
CAS No.:1289117-14-1
Molecular Formula:C₁₉H₂₈O₃SSi
Molecular Weight:364.581
Hs Code.:

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

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

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

There total 2 articles about (+)-(1R,3R,5S,6S)-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: 98.0%

: 887404-60-6
(4S,6R)-4-(tert-butyldimethylsilyloxy)-6-methyl-6-phenylthiocyclohex-2-enone

: 1289117-14-1
(+)-(1R,3R,5S,6S)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃;
DOI:10.1002/ejoc.201001527

Reference yield:

: 697741-20-1
(4S)-4-(tert-butyldimethylsilyloxy)-10-phenylthiocyclohex-2-enone

: 1289117-14-1
(+)-(1R,3R,5S,6S)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: 1.25 h / -78 - 20 °C / Inert atmosphere

2.1: tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide / tetrahydrofuran; water / 0 - 20 °C

With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; sodium hydride; In tetrahydrofuran; water;
DOI:10.1002/ejoc.201001527

Reference yield:

: 1289117-14-1
(+)-(1R,3R,5S,6S)-5-(tert-butyldimethylsilyloxy)-3-methyl-3-(phenylthio)-7-oxabicyclo[4.1.0]heptan-2-one

: 1204745-26-5
(+)-gabosine A

Guidance literature:: Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1 h / 0 °C

1.2: 12 h / 20 °C

2.1: dmap / acetonitrile / 0.08 h / 0 - 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / toluene / 2 h / 0 °C

3.2: 1 h / 20 °C

With dmap; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In chloroform; toluene; acetonitrile;
DOI:10.1002/ejoc.201001527