17663-43-3

Usage

Uses

Used in Chemical Synthesis:
D-Proline, 3,4-dihydroxy-, (3S,4R)-rel(9CI) is used as a building block in various chemical synthesis processes. Its unique structure and functional groups make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
D-Proline, 3,4-dihydroxy-, (3S,4R)-rel(9CI) is used as a key intermediate in the development of pharmaceutical compounds, particularly in the synthesis of dihydroxylated prolines and iminocyclitols. These synthesized compounds have potential applications as glycosidase inhibitors, which can be utilized in the treatment of various diseases, such as cancer and infectious diseases.
Used in Research and Development:
Due to its unique stereochemistry and functional groups, D-Proline, 3,4-dihydroxy-, (3S,4R)-rel(9CI) is also used in research and development for studying the structure-activity relationships of proline derivatives and their potential biological activities. This can lead to the discovery of new drugs and therapeutic agents.

Upstream product

• 141366-40-7 1-benzyl-(2SR)-(methoxycarbonyl)pyrrolidine-(3SR,4RS)-diyl carbonate 
• 141366-39-4 (2SR)-methoxycarbonyl-1-tosylpyrrolidine-(3SR,4RS)-diyl carbonate 
• 17645-37-3 (2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol 
• 141366-40-7 1-benzyl-(2RS)-(methoxycarbonyl)pyrrolidine-(3SR,4RS)-diyl carbonate 
• 141366-39-4 (2RS)-methoxycarbonyl-1-tosylpyrrolidine-(3SR,4RS)-diyl carbonate 
• 138228-39-4 (3S,4S)-3,4-dibenzoyloxy-2-cyanopyrrolidine 
• 17645-37-3 (2RS)-hydroxymethyl-1-tosylpyrrolidine-(3SR,4RS)-diol 

Downstream Products

• 138228-51-0 (2S,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 
• 138228-52-1 (2R,3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxy-2-methoxycarbonylpyrrolidine 

Relevant academic research and scientific papers

Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.

Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate

A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrro

(±)-4-amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams

Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regioselectivity to the oxazine adducts 5a,b. Sequential osmylation, protection of the ensuing glycol, and reduction of th

DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES FOR THE SYNTHESIS OF POLYHYDROXYPYRROLIDINES AS POTENTIAL ENZYMATIC INHIBITORS

Tosyl and benzyl azomethine ylides generated from the corresponding aziridines under thermal and photochemical conditions, were trapped by dipolar cycloaddition reaction with vinylene carbonate.The methoxycarbonyl group in the pyrrolidines obtained was re

Synthesis of (3S,4S)-3,4-dihydroxyprolines from L-tartaric acid

Natural (2S,3S,4S)-3,4-dihydroxyproline (1) and the new (2R,3S,4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.