Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

Base Information

Chemical Name:Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate
CAS No.:162264-90-6
Molecular Formula:C₃₁H₃₆O₅SSi
Molecular Weight:548.775
Hs Code.:

Synonyms:Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

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Chemical Property of Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

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Technology Process of Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

There total 3 articles about Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-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: 95.0%

: methyl (4R)-4-[(phenylthio)-acetoxy]-6-tert-butyldiphenylsilyloxy-hexen-2(E)-oate

: 162264-90-6
Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; paraffin; at -50 ℃; for 4h;
DOI:10.1021/jo00095a022

Reference yield:

: 920502-51-8
(2S,3R)-1,2-dihydro-5-tertbutyldiphenylsilyloxy-pentan-3-yl 2-(phenylthio)acetate

: 162264-90-6
Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaIO₄; tetrabutylammonium periodate / methanol; H₂O / 1 h / 20 °C

1.2: 76 percent / sodium hydride / benzene / 0.5 h

2.1: 95 percent / sodium hydride / dimethylformamide / 4 h

With sodium periodate; sodium hydride; tetrabutylammonium periodite; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

: 116003-84-0
(2S,3S)-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)-2-oxiranyl)methan-1-ol

: 162264-90-6
Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 80 percent / Ti(OPr-i)4 / CH₂Cl₂ / 2 h / 20 °C

2.1: NaIO₄; tetrabutylammonium periodate / methanol; H₂O / 1 h / 20 °C

2.2: 76 percent / sodium hydride / benzene / 0.5 h

3.1: 95 percent / sodium hydride / dimethylformamide / 4 h

With titanium(IV) isopropylate; sodium periodate; sodium hydride; tetrabutylammonium periodite; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.jorganchem.2006.08.021