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

Base Information

Chemical Name:(1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxycyclopentanecarboxylate
CAS No.:384343-92-4
Molecular Formula:C₂₇H₄₈O₅SSi₂
Molecular Weight:540.912
Hs Code.:

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

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Chemical Property of (1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxycyclopentanecarboxylate

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Technology Process of (1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxycyclopentanecarboxylate

There total 5 articles about (1R,2R,3S,4R,5R)-ethyl 2-benzylsulfanyl-3,5-bis(tert-butyldimethylsiloxy)-4-hydroxycyclopentanecarboxylate 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: 41.0%

: 100-53-8
phenylmethanethiol

: 384343-89-9
(4R,5S)-4,5-bis-(tert-butyldimethylsilanyloxy)-6-oxohex-2-(E)-enoic acid ethyl ester

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

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

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

Guidance literature:: With n-butyllithium; In 1,4-dioxane; hexane; at 20 ℃; for 0.5h;
DOI:10.1021/jo016090n

Reference yield:

: 384343-82-2
(E)-ethyl 3-[(4R,5R)-5-(4-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate

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

Guidance literature:: Multi-step reaction with 5 steps

1: 2 N HCl / ethanol / 1.5 h / 40 °C

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 3.79 g / DDQ / CH₂Cl₂; H₂O / 1.33 h / 20 °C

4: 86 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

5: 28 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 4: Swern oxidation;
DOI:10.1021/jo016090n

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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