(3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

Base Information

Chemical Name:(3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate
CAS No.:384343-93-5
Molecular Formula:C₁₈H₂₄O₅S
Molecular Weight:352.452
Hs Code.:

Synonyms:(3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

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Chemical Property of (3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

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Technology Process of (3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

There total 8 articles about (3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate 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: 89.0%

: 67-64-1
acetone

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

: 384343-93-5
(3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; at 20 ℃; for 4h;
DOI:10.1021/jo016090n

Reference yield:

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

: 384343-93-5
(3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

Guidance literature:: Multi-step reaction with 6 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

6: 89 percent / p-TsOH*H₂O / 4 h / 20 °C

With n-butyllithium; oxalyl dichloride; hydrogen fluoride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 3: Swern oxidation;
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

: 384343-93-5
(3aR,4R,5R,6S,6aS)-ethyl 5-benzylsulfanyl-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[1,3]dioxole-4-carboxylate

Guidance literature:: Multi-step reaction with 7 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

6: 99 percent / aq. HF / acetonitrile / 3 h / 0 °C

7: 89 percent / p-TsOH*H₂O / 4 h / 20 °C

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