(3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile

Base Information

• Chemical Name: (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile
• CAS No.: 101514-20-9
• Molecular Formula: C₁₉H₁₉NO₂S
• Molecular Weight: 325.431
• Mol file: 101514-20-9.mol

Synonyms:(3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile

Chemical Property of (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile

There total 12 articles about (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile 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: 50.0%

(S)-2-((R)-1-Benzyloxy-2-bromo-ethyl)-oxirane (101514-16-3) → (S)-2-(1-Benzyloxy-vinyl)-oxirane (101514-19-6) + (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile (101514-20-9)

Guidance literature:

With n-butyllithium; (phenylthio)acetonitrile; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)98634-9

Reference yield: 30.0%

(S)-2-((R)-1-Benzyloxy-2-chloro-ethyl)-oxirane (101514-17-4) → (S)-2-(1-Benzyloxy-vinyl)-oxirane (101514-19-6) + (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile (101514-20-9)

Guidance literature:

With n-butyllithium; (phenylthio)acetonitrile; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)98634-9

Reference yield:

dimethyl 2,3-O-benzylidene-L-tartrate (38270-72-3) → (3S,4S)-3-Benzyloxy-4-hydroxy-1-phenylsulfanyl-cyclopentanecarbonitrile (101514-20-9)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / bis-(2-methoxy-ethyl) ether

3: LiBr / bis-(2-methoxy-ethyl) ether

4: Na(CN)BH₃ / acetonitrile

5: NaOMe / methanol

6: 1.) n-BuLi / 2.) ether, TMEDA, 0 deg C

With sodium tetrahydroborate; n-butyllithium; sodium methylate; sodium cyanoborohydride; lithium bromide; In methanol; diethylene glycol dimethyl ether; acetonitrile;

DOI:10.1016/S0040-4039(00)98634-9

upstream raw materials:

(phenylthio)acetonitrile

(S)-2-((R)-1-Benzyloxy-2-chloro-ethyl)-oxirane

(S)-2-((R)-1-Benzyloxy-2-bromo-ethyl)-oxirane

Toluene-4-sulfonic acid (S)-2-benzyloxy-2-(S)-oxiranyl-ethyl ester

Downstream raw materials:

1-cyano-1-thiophenyl-3,4-dibenzyloxycyclopentane