163439-83-6

Basic information

• Product Name: (+)-(3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine
• Synonyms: (3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-pyrrolidine; (3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine; (R,R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine; benzyl (3R,4R)-3,4-dihydroxypyrrolidine-1-carboxylate
• CAS NO: 163439-83-6
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25200
• Mol File: 163439-83-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (+)-(3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine(163439-83-6)
• EPA Substance Registry System: (+)-(3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine(163439-83-6)

Safety Data

• Hazardous Substances Data: 163439-83-6(Hazardous Substances Data)

Usage

General Description

(+)-(3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine is a chemical compound with the molecular formula C15H19NO4. It is a pyrrolidine derivative that is commonly used in organic synthesis and drug development. The compound contains both a benzyloxycarbonyl (Cbz) group and two hydroxyl groups attached to a pyrrolidine ring. The benzyloxycarbonyl group serves as a protective group for the amine functionality, allowing for selective manipulation of the compound in various synthetic reactions. The presence of the hydroxyl groups also provides potential for further modification, making (+)-(3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxypyrrolidine a versatile building block for the synthesis of complex organic molecules and pharmaceuticals.

Upstream product

• 31865-25-5 benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 31970-04-4 1-carboxybenzyl-3-pyrrolidine 
• 141-78-6 ethyl acetate 
• 501-53-1 benzyl chloroformate 
• 186393-31-7 (3R,4R)-pyrrolidine-3,4-diol 

Downstream Products

• 163400-67-7 (3R,4R)-3-Hydroxy-4-(4-methoxy-benzyloxy)-pyrrolidine-1-carboxylic acid benzyl ester 
• 186393-31-7 (3R,4R)-pyrrolidine-3,4-diol 
• 596794-44-4 benzyl (3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-carboxylate 

Relevant articles and documents

Enantioselective hydrolysis of racemic and meso -epoxides with recombinant escherichia coli expressing epoxide hydrolase from Sphingomonas sp. HXN-200: Preparation of epoxides and vicinal diols in high ee and high concentration

A unique epoxide hydrolase (SpEH) from Sphingomonas sp. HXN-200 was identified and cloned based on genome sequencing and expressed in Escherichia coli. The engineered E. coli (SpEH) showed the same selectivity and substrate specificity as the wild type strain and 172 times higher activity than Sphingomonas sp. HXN-200 for the hydrolysis of styrene oxide 1. Hydrolysis of racemic styrene oxide 1, substituted styrene oxides 3, 5-7, and N-phenoxycarbonyl-3,4-epoxypiperidine 8 (200-100 mM) with resting cells of E. coli (SpEH) gave (S)-epoxides 1, 3, 5-7 and (-)-8 in 98.0-99.5% enantiomeric excess (ee) and 37.6-46.5% yield. Hydrolysis of cyclopentene oxide 9, cyclohexene oxide 10, and N-benzyloxycarbonyl-3,4-epoxypyrrolidine 11 (100 mM) afforded the corresponding (R, R)-vicinal trans-diols 12-14 in 86-93% ee and 90-99% yield. The ee of (1R, 2R)-cyclohexane-1,2-diol 13 was improved to 99% by simple crystallization. These biotransformations showed high specific activity (0.28-4.3 U/mg cdw), product concentration, product/cells ratio, and cell-based productivity. Hydrolysis at even higher substrate concentration was also achieved: (S)-1 was obtained in 430 mM (51 g/Lorg) and 43% yield; (1R, 2R)-13 was obtained in 500 mM (58 g/L) and >99% yield. Gram-scale preparation of epoxides (S)-1, (S)-3, (S)-6 and diols (1R, 2R)-12, (1R, 2R)-13, (3R, 4R)-14 were also demonstrated. E. coli (SpEH) cells showed the highest enantioselectivity to produce (S)-1 (E of 39) among all known EHs in the form of whole cells or free enzymes and the highest enantioselectivities to produce (S)-3, 5, 6, 7, (-)-8, and (R, R)-14 (E of 36, 35, 28, 57, 22, and 28) among all known EHs. The easily available and highly active E. coli (SpEH) cells are the best biocatalysts known thus far for the practical preparation of these useful and valuable enantiopure epoxides and vicinal diols via hydrolysis.

Biocatalytic preparation of chiral 3,4-dihydroxypyrrolidines

Enzymatic acylations and alcoxycarbonylations of cis- and trans-3,4-dihydroxypyrrolidines and hydrolysis of their diacylated or dialcoxycarbonylated derivatives have been studied. High enantioselectivity is obtained using Candida antarctica lipase B as catalyst in the hydrolysis of the trans-diacetyl derivative, while for the desymmetrization of the cis-3,4-dihydroxypyrrolidines the best results are obtained in the acylation process catalyzed by C. antarctica lipase A.

Fluoropyrrolidine amides as dipeptidyl peptidase IV inhibitors

Amides derived from fluorinated pyrrolidines and 4-substituted cyclohexylglycine analogues have been prepared and evaluated as inhibitors of dipeptidyl dipeptidase IV (DP-IV). Analogues which incorporated (S)-3-fluoropyrrolidine showed good selectivity for DP-IV over quiescent cell proline dipeptidase (QPP). Compound 48 had good pharmacokinetic properties and was orally active in an oral glucose tolerance test in lean mice.