(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

Base Information

Chemical Name:(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid
CAS No.:920502-59-6
Molecular Formula:C₃₁H₃₆O₅SSi
Molecular Weight:548.775
Hs Code.:

Synonyms:(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

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Chemical Property of (2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

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Technology Process of (2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

There total 4 articles about (2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid 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: 90.0%

: 920502-55-2
methyl 2-(2R,3R,4S)-5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl-acetate

: 920502-59-6
(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; water;
DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

: 920502-52-9
(2S,3R)-1,2-dihydro-6-tert-butyldiphenylsilyloxy-hexan-3-yl 2-(phenylthio)acetate

: 920502-59-6
(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 74 percent / sodium hydride / benzene / 0.5 h

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

3.1: 90 percent / NaOH / tetrahydrofuran; H₂O

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

Reference yield:

: 920502-53-0
methyl (4R)-4-[(phenylthio)-acetoxy]-7-tert-butyldiphenylsilyloxy-hepten-2(E)-oate

: 920502-59-6
(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(3-tert-butyldiphenylsilyloxy)propyl-tetrahydrofuran-3-yl]acetic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / sodium hydride / dimethylformamide / 4 h

2: 90 percent / NaOH / tetrahydrofuran; H₂O

With sodium hydroxide; sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1016/j.jorganchem.2006.08.021