(3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

Base Information

Chemical Name:(3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester
CAS No.:362471-97-4
Molecular Formula:C₁₆H₁₈O₅S
Molecular Weight:322.382
Hs Code.:

Synonyms:(3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

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Chemical Property of (3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

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Technology Process of (3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

There total 3 articles about (3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester 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: 55.0%

: 121542-25-4
(1S,2S,3S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-ethoxycarbonylmethyl-5-phenylsulfanyl-cyclopentanecarboxylic acid ethyl ester

: 362471-97-4
(3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

Guidance literature:: (1S,2S,3S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-ethoxycarbonylmethyl-5-phenylsulfanyl-cyclopentanecarboxylic acid ethyl ester; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.75h;

With toluene-4-sulfonic acid; In benzene; at 20 ℃; for 1h;
DOI:10.1016/S0957-4166(01)00213-0

Reference yield:

: 121542-15-2
Diethyl (4S,5S)-4,5-bis(tert-butyldimethylsilyloxy)-(2E,6E)-octadienedioate

: 362471-97-4
(3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / n-BuLi / 3 h / -78 - -40 °C

2.1: Bu₄NF / tetrahydrofuran / 0.75 h

2.2: 55 percent / p-toluenesulfonic acid / benzene / 1 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1.1: tandem Michael reaction;
DOI:10.1016/S0957-4166(01)00213-0

Reference yield:

: 108-98-5
thiophenol

: 362471-97-4
(3aS,4S,5S,6R,6aS)-6-Hydroxy-2-oxo-5-phenylsulfanyl-hexahydro-cyclopenta[b]furan-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / n-BuLi / 3 h / -78 - -40 °C

2.1: Bu₄NF / tetrahydrofuran / 0.75 h

2.2: 55 percent / p-toluenesulfonic acid / benzene / 1 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1.1: tandem Michael reaction;
DOI:10.1016/S0957-4166(01)00213-0