(3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine

Base Information

• Chemical Name: (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine
• CAS No.: 596793-30-5
• Molecular Formula: C12H15 N O4
• Molecular Weight: 237.255
• Mol file: 596793-30-5.mol

Synonyms:(3S,4S)-Benzyl 3,4-dihydroxypyrrolidine-1-carboxylate; (3S,4S)-3,4-Dihydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester

Chemical Property of (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine

Chemical Property:

• PSA: 70.00000
• Density: 1.378
• LogP: 0.29850
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

(3S,4S)-Benzyl3,4-dihydroxypyrrolidine-1-carboxylate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine

There total 7 articles about (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine 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:

(3S,4S)-pyrrolidine-3,4-diol (90481-32-6) + benzyl chloroformate (501-53-1,94274-21-2) → (3S,4S)-N-benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine (596793-30-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2003.12.040

Reference yield:

(1R,5S)-benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate → (+)-(3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxypyrrolidine (163439-83-6) + (3S,4S)-N-benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine (596793-30-5)

Guidance literature:

With BD₉₈₈₄; In phosphate buffer; acetonitrile; at 22 ℃; pH=7.5; Title compound not separated from byproducts;

DOI:10.1021/ja0466210

Reference yield:

benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (31865-25-5) → (+)-(3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxypyrrolidine (163439-83-6) + (3S,4S)-N-benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine (596793-30-5)

Guidance literature:

With D-glucose; Sphingomonas sp. HXN-200 epoxide hydrolase; In phosphate buffer; at 30 ℃; for 5h; pH=8.0; Title compound not separated from byproducts;

DOI:10.1039/b300435j

upstream raw materials:

benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

(3S,4S)-pyrrolidine-3,4-diol

benzyl chloroformate

1-carboxybenzyl-3-pyrrolidine

Downstream raw materials:

3S,4S-dimethoxy-pyrrolidine-1-carboxylic acid benzyl ester

N-(benzyloxycarbonyl)iminodiacetaldehyde

3a,7a-Dihydroxy-octahydro-4,8-dioxa-2,6-diaza-s-indacene-2,6-dicarboxylic acid di-benzyl ester

(3R,4R)-3,4-Difluoro-pyrrolidine-1-carboxylic acid benzyl ester

Refernces

• 1、 -. "COFERONS AND METHODS OF MAKING AND USING THEM". Page/Page column 170. . Retrieved 2012/12/13.
• 2、 Caldwell, Charles G.,Chen, Ping,He, Jiafang,Parmee, Emma R.,Leiting, Barbara,Marsilio, Frank,Patel, Reshma A.,Wu, Joseph K.,Eiermann, George J.,Petrov, Aleksandr,He, Huaibing,Lyons, Kathryn A.,Thornberry, Nancy A.,Weber, Ann E.. "Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors". . p. 1265 - 1268. Retrieved 2007/10/03.