(3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
• CAS No.: 712281-35-1
• Molecular Formula: C₂₁H₂₇ClN₂O₄S
• Molecular Weight: 438.975
• Mol file: 712281-35-1.mol

Synonyms:

Chemical Property of (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

There total 3 articles about (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl 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:

N-tert-butoxycarbonyl-3,6-imino-4,5-O-isopropylidene-2,3,6-trideoxy-D-allo-heptononitrile (222631-50-7) → (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (712281-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

2.1: sodium hydride / dimethylformamide

2.2: dimethylformamide / 3 h

With sodium hydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0306475

Reference yield:

(3aR,4R,6S,6aS)-tert-butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(cyanomethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate (222631-09-6) → (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (712281-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h

2.1: 90 percent / diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

3.1: sodium hydride / dimethylformamide

3.2: dimethylformamide / 3 h

With tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0306475

Reference yield:

p-Chlorothiophenol (106-54-7) + N-tert-butoxycarbonyl-3,6-imino-4,5-O-isopropylidene-7-O-methanesulfonyl-2,3,6-trideoxy-D-allo-heptononitrile (607389-13-9) → (3aR,4S,6S,6aS)-4-(4-Chloro-phenylsulfanylmethyl)-6-cyanomethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (712281-35-1)

Guidance literature:

p-Chlorothiophenol; With sodium hydride; In N,N-dimethyl-formamide;

N-tert-butoxycarbonyl-3,6-imino-4,5-O-isopropylidene-7-O-methanesulfonyl-2,3,6-trideoxy-D-allo-heptononitrile; In N,N-dimethyl-formamide; for 3h;

DOI:10.1021/jm0306475

upstream raw materials:

p-Chlorothiophenol

N-tert-butoxycarbonyl-3,6-imino-4,5-O-isopropylidene-7-O-methanesulfonyl-2,3,6-trideoxy-D-allo-heptononitrile

N-tert-butoxycarbonyl-3,6-imino-4,5-O-isopropylidene-2,3,6-trideoxy-D-allo-heptononitrile

(3aR,4R,6S,6aS)-tert-butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(cyanomethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate