155935-60-7

Basic information

• Product Name: 2,4-Pyrrolidinedimethanol,3-amino-,(2R,3R,4R)-(9CI)
• Synonyms: 2,4-Pyrrolidinedimethanol,3-amino-,(2R,3R,4R)-(9CI)
• CAS NO: 155935-60-7
• Molecular Formula: C₆H₁₄N₂O₂
• Molecular Weight: 146.19
• Product Categories: AMINEPRIMARY
• Mol File: 155935-60-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Pyrrolidinedimethanol,3-amino-,(2R,3R,4R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pyrrolidinedimethanol,3-amino-,(2R,3R,4R)-(9CI)(155935-60-7)
• EPA Substance Registry System: 2,4-Pyrrolidinedimethanol,3-amino-,(2R,3R,4R)-(9CI)(155935-60-7)

Safety Data

• Hazardous Substances Data: 155935-60-7(Hazardous Substances Data)

Usage

Structure

Pyrrolidine ring with two hydroxyl groups and an amino group attached to the third carbon

Chiral center

One

Stereoisomers

Exists as a pair of enantiomers with (2R,3R,4R) configuration being one of the possible stereoisomers

Applications

Potential use in pharmaceutical and chemical industries for asymmetric synthesis, as a chiral resolving agent, and as a building block for the synthesis of various organic compounds.

Upstream product

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• 155935-64-1 (6R,7R,7aR)-7-Amino-6-hydroxymethyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 

Relevant articles and documents

IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L- serine.

Utilization of L-serine in an oxime olefin cycloaddition route to a functionalized asymmetric pyrrolidine, a selective α-glucosidase inhibitor

A new route for asymmetric aza-sugar analogs starting with L-serine and utilizing an intramolecular oxime olefin cycloaddition has been successfully developed. A member of this family of branched chain sugar amino di(hydroxymethyl) pyrrolidines (1 and 2) exhibits selective inhibition of α-glucosidase, while no inhibition of β-glucosidase was detected.