(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

Base Information

Chemical Name:(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one
CAS No.:106820-44-4
Molecular Formula:C₂₅H₃₄O₃S₃Si
Molecular Weight:506.827
Hs Code.:

Synonyms:(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

Suppliers and Price of (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

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Chemical Property of (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

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Technology Process of (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

There total 11 articles about (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-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: 86.0%

: 39090-54-5
tris(methylthio)methyl lithium

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 106820-44-4
(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1021/jo00382a043

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 106820-44-4
(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

With dmap; n-butyllithium; dihydrogen peroxide; triethylamine; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 5418-86-0
tris(methylthio)methane

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 106820-44-4
(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one

Guidance literature:: With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.;
DOI:10.1016/S0040-4020(01)87683-3