596793-30-5

Basic information

• Product Name: (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine
• Synonyms: (3s,4s)-n-cbz-3,4-dihydroxypyrrolidine;(3S,4S)-3,4-Dihydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester;(3S,4S)-Benzyl 3,4-dihydroxypyrrolidine-1-carboxylate;N-Cbz-(3S,4S)-dihydroxypyrrolidine-1-carboxylate
• CAS NO: 596793-30-5
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• Mol File: 596793-30-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.378
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine(596793-30-5)
• EPA Substance Registry System: (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine(596793-30-5)

Safety Data

• Hazardous Substances Data: 596793-30-5(Hazardous Substances Data)

Usage

General Description

(3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine is a chemical compound with a molecular formula C13H18N2O3. It is a derivative of pyrrolidine and is commonly used in the synthesis of various pharmaceutical compounds. (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine is chiral, with two stereocenters at the 3 and 4 positions, leading to four possible stereoisomers. It is often used as a building block in organic synthesis and is known for its ability to form amines and amides through various chemical reactions. Additionally, (3S,4S)-N-Cbz-3,4-dihydroxypyrrolidine has been studied for its potential use in the development of new drug molecules due to its unique structure and reactivity.

InChI:InChI=1/C12H15NO4/c14-10-6-13(7-11(10)15)12(16)17-8-9-4-2-1-3-5-9/h1-5,10-11,14-15H,6-8H2/t10-,11-/m0/s1

Upstream product

• 31865-25-5 benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 90481-32-6 (3S,4S)-pyrrolidine-3,4-diol 
• 141-78-6 ethyl acetate 
• 31970-04-4 1-carboxybenzyl-3-pyrrolidine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 127747-10-8 N-(benzyloxycarbonyl)iminodiacetaldehyde 
• 1290056-27-7 3a,7a-Dihydroxy-octahydro-4,8-dioxa-2,6-diaza-s-indacene-2,6-dicarboxylic acid di-benzyl ester 
• 596793-31-6 3S,4S-dimethoxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 790658-58-1 (3R,4R)-3,4-Difluoro-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis of Three-Dimensional (Di)Azatricyclododecene Scaffold and Its Application to Peptidomimetics

A novel sp3 carbon-rich tricyclic 3D scaffold-based peptide mimetic compound library was constructed to target protein-protein interactions. Tricyclic framework 7 was synthesized from 9-azabicyclo[3,3,1]nonan-3-one (11) via a gold(I)-catalyzed Conia-ene reaction. The electron-donating group on the pendant alkyne of cyclization precursor 12 b–e was the key to forming 6-endo-dig cyclized product 7 with complete regioselectivity. Using the synthetic strategy for regioselective construction of bridged tricyclic framework 7, a diazatricyclododecene 3D-scaffold 8 a, which enables the introduction of substituents into the scaffold to mimic amino acid side chains, was designed and synthesized. The peptide mimetics 21 a–u were synthesized via step-by-step installation of three substituents on diazatricyclododecene scaffold 8 a. Compounds 21 a–h were synthesized as α-helix peptide mimics of hydrophobic ZZxxZ and ZxxZZ sequences (Z=Leu or Phe) and subjected to cell-based assays: antiproliferative activity, HIF-1 transcriptional activity which is considered to affect cancer malignancy, and antiviral activity against rabies virus. Compound 21 a showed the strongest inhibitory activity of HIF-1 transcriptional activity (IC50=4.1±0.8 μM), whereas compounds 21 a–g showed antiviral activity with IC50 values of 4.2–12.4 μM, suggesting that the 3D-scaffold 8 a has potential as a versatile peptide mimic skeleton.

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.