(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

Base Information

Chemical Name:(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate
CAS No.:384343-96-8
Molecular Formula:C₁₅H₂₀O₅S
Molecular Weight:312.387
Hs Code.:

Synonyms:(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

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Chemical Property of (1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

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Technology Process of (1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

There total 7 articles about (1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate 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: 99.0%

: 384343-91-3
(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4-bis(tert-butyldimethylsiloxy)-5-hydroxycyclopentanecarboxylate

: 384343-96-8
(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃; for 3h;
DOI:10.1021/jo016090n

Reference yield: 99.0%

: 384343-92-4
(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxycyclopentanecarboxylate

: 384343-96-8
(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃; for 3h;
DOI:10.1021/jo016090n

Reference yield:

: 384343-86-6
(E)-ethyl (4R,5R)-4,5-dihydroxy-6-(4-methoxybenzyloxy)hex-2-enoate

: 384343-96-8
(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,4,5-trihydroxycyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 3.79 g / DDQ / CH₂Cl₂; H₂O / 1.33 h / 20 °C

3: 86 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

4: 28 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C

5: 99 percent / aq. HF / acetonitrile / 3 h / 0 °C

With n-butyllithium; oxalyl dichloride; hydrogen fluoride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 3: Swern oxidation;
DOI:10.1021/jo016090n