(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Base Information

Chemical Name:(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one
CAS No.:920502-57-4
Molecular Formula:C₃₀H₃₆O₄SSi
Molecular Weight:520.765
Hs Code.:

Synonyms:(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

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Chemical Property of (3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

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Technology Process of (3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

There total 5 articles about (3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-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%

: 920502-56-3
(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(2-tert-butyldiphenylsilyloxy)ethyl-tetrahydrofuran-3-yl]acetic acid

: 920502-57-4
(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran;
DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

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

: 920502-57-4
(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Guidance literature:: Multi-step reaction with 4 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

3.1: 92 percent / NaOH / tetrahydrofuran; H₂O

4.1: 86 percent / BH₃*SMe₂ / tetrahydrofuran

With sodium hydroxide; sodium periodate; dimethylsulfide borane complex; sodium hydride; tetrabutylammonium periodite; In tetrahydrofuran; 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

: 920502-57-4
(3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 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

4.1: 92 percent / NaOH / tetrahydrofuran; H₂O

5.1: 86 percent / BH₃*SMe₂ / tetrahydrofuran

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