849935-87-1

Usage

Uses

Used in Pharmaceutical Industry:
(3S,4S)-1-Boc-3-hydroxy-4-(hydroxymethyl)-pyrrolidine is used as a building block for the preparation of various drug molecules and related compounds. Its unique structure and functional groups contribute to the synthesis of complex organic molecules, enhancing the development of novel pharmaceuticals.
Used in Organic Synthesis:
(3S,4S)-1-Boc-3-hydroxy-4-(hydroxymethyl)-pyrrolidine is used as a versatile intermediate in organic synthesis. Its Boc-protected hydroxy group provides selectivity and stability in chemical reactions, making it a valuable tool for the synthesis of a wide range of organic compounds.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 397883-77-1 (3S,4S)-3-hydroxy-4-hydroxymethylpyrrolidine 
• 71336-69-1 (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate 
• 849935-80-4 (3S,4S)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol 

Downstream Products

• 1609403-89-5 (3S,4S)-4-(hydroxymethyl)pyrrolidin-3-ol hydrochloride 

Relevant academic research and scientific papers

Catalytic discrimination between formyl groups in regio-and stereoselective intramolecular cross-Aldol reactions

Catalytic discrimination between inequivalent formyl groups was achieved using an aniline-Type acid-base catalyst for the regio-, diastereo-, and enantioselective intramolecular cross-Aldol reactions of enolizable dials. Although l-proline gave a mixture of the regio-and stereoisomeric products in the presence of an N-containing 1,6-dial, the aniline-Type catalyst afforded anti-3,4-disubstituted pyrrolidine in high regio-, and stereoselectivity beyond the background reaction, which led to the regioisomeric 2,3-disubstituted products. The mild reactivity of the aniline-Type amine facilitated catalytic discrimination between the inequivalent formyl groups. Kinetic isotope effect studies and reductive amination experiments suggested that the regioselectivity was controlled under the enamine-forming steps.

Tight binding enantiomers of pre-clinical drug candidates

MTDIA is a picomolar transition state analogue inhibitor of human methylthioadenosine phosphorylase and a femtomolar inhibitor of Escherichia coli methylthioadenosine nucleosidase. MTDIA has proven to be a non-toxic, orally available pre-clinical drug candidate with remarkable anti-tumour activity against a variety of human cancers in mouse xenografts. The structurally similar compound MTDIH is a potent inhibitor of human and malarial purine nucleoside phosphorylase (PNP) as well as the newly discovered enzyme, methylthioinosine phosphorylase, isolated from Pseudomonas aeruginosa. Since the enantiomers of some pharmaceuticals have revealed surprising biological activities, the enantiomers of MTDIH and MTDIA, compounds 1 and 2, respectively, were prepared and their enzyme binding properties studied. Despite binding less tightly to their target enzymes than their enantiomers compounds 1 and 2 are nanomolar inhibitors.

METHOD FOR PREPARING 3-HYDROXY-4-HYDROXYMETHYL-PYRROLIDINE COMPOUNDS

This invention relates to a method of preparing (3R,4R)-3-hydroxy-4-hydroxymethylpyrrolidine, a key intermediate compound for the synthesis of certain inhibitor compounds, including the step of enzyme catalysed enantioselective esterification of an hydroxy group of an hydroxypyrrolidine. The invention further relates to a method for preparing (3S,4S)-3-hydroxy-4-hydroxymethylpyrrolidine, which is the enantiomer of (3R,4R)-3-hydroxy-4-hydroxymethylpyrrolidine.