1262015-07-5

Basic information

• Product Name: (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester
• Synonyms: (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester;Cbz-cis-3-Hydroxy-L-proline
• CAS NO: 1262015-07-5
• Molecular Formula: C₁₃H₁₅NO₅
• Molecular Weight: 265.2619
• Mol File: 1262015-07-5.mol

Chemical Properties

• Boiling Point: 486.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.416±0.06 g/cm3(Predicted)
• PKA: 3.67±0.40(Predicted)
• CAS DataBase Reference: (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester(1262015-07-5)
• EPA Substance Registry System: (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester(1262015-07-5)

Safety Data

• Hazardous Substances Data: 1262015-07-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester is used as a building block for the synthesis of various pharmaceuticals and organic compounds. Its unique chemical structure and properties make it a promising candidate for drug discovery and development.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester is utilized as a versatile intermediate for the synthesis of biologically active molecules, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
(2S,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylMethyl) ester is employed as a key intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds and materials.

Upstream product

• 107690-61-9 3,6-epimino-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 98944-20-8 (1R,3R,7R,8S)-9-<(benzyloxy)carbonyl>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane 
• 1290130-76-5 C₁₄H₁₅NO₅ 

Downstream Products

• 567-35-1 (2S,3R)-3-hydroxyproline 
• 496841-08-8 cis-3-hydroxy-L-proline methyl ester 

Relevant articles and documents

D-Glucose based syntheses of β-hydroxy derivatives of l-glutamic acid, l-glutamine, l-proline and a dihydroxy pyrrolidine alkaloid

The β-hydroxy derivatives of l-glutamic acid, l-glutamine and l-proline, useful for peptide/protein studies, were synthesized starting from d-glucose. The C2 carbon in d-glucose provided the carboxylic acid functionality, while the amino and β-hydroxy groups of the amino acids were amenable from the C3 and C4 hydroxy groups of the sugar, respectively. The key intermediate with appropriate carbon framework of the target molecules was constructed by homologation of a suitable azido-d-glucofuranose derivative using the Arndt-Eistert reaction. This journal is

Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose

Synthesis of cis-3-hydroxy-l-proline from d-glucose is reported. The methodology involves conversion of d-glucose into N-benzyloxycarbonyl-γ- alkenyl amine which on 5-endo-trig-aminomercuration gave the pyrrolidine ring skeleton with sugar appendage in 25% yield. Alternatively, N-benzyloxycarbonyl- γ-alkenyl amine on hydroboration-oxidation, mesylation and intramolecular SN2 cyclisation afforded pyrrolidine ring compound in high yield. Hydrolysis of 1,2-acetonide functionality, NaIO4 cleavage followed by oxidation of an aldehyde into acid and hydrogenolysis afforded cis-3-hydroxy-l-proline in overall 29% yield from d-glucose.