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

Base Information

Chemical Name:(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate
CAS No.:529495-86-1
Molecular Formula:C₂₇H₃₈O₄S₃Si
Molecular Weight:550.88
Hs Code.:

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

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

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

There total 3 articles about (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate 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: 70.0%

: 75-36-5
acetyl chloride

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

: 529495-86-1
(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

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

: 529495-86-1
(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2: DIBAL / toluene; hexane / 1 h / -70 °C

3: 70 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/S0968-0896(02)00460-1

Reference yield:

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

: 529495-86-1
(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: DIBAL / toluene; hexane / 1 h / -70 °C

2: 70 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; diisobutylaluminium hydride; In hexane; dichloromethane; toluene;
DOI:10.1016/S0968-0896(02)00460-1