141410-49-3

Basic information

• Product Name: (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol
• Synonyms: (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS NO: 141410-49-3
• Molecular Weight: 223.272
• Mol File: 141410-49-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol(141410-49-3)
• EPA Substance Registry System: (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol(141410-49-3)

Safety Data

• Hazardous Substances Data: 141410-49-3(Hazardous Substances Data)

Upstream product

• 132430-67-2 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol 
• 177493-30-0 5-O-(tert-butyldimethylsilyl)-1,4-bis(methanesulfonyl)-2,3-di-O-isopropylidene-D-ribitol 
• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 84709-46-6 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 177493-29-7 5-O-(tert-butyldimethylsilyl)2,3-di-O-isopropylidene-D-ribitol 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 177569-79-8 (3aR,4S,6aS)-5-benzyl-4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 100-46-9 benzylamine 

Downstream Products

• 129568-47-4 (2S,3R,4S)-2-hydroxymethyl-pyrrolidine-3,4-diol 

Relevant articles and documents

N-Benzyl Substitution of Polyhydroxypyrrolidines: The Way to Selective Inhibitors of Golgi α-Mannosidase II

Inhibition of the biosynthesis of complex N-glycans in the Golgi apparatus influences progress of tumor growth and metastasis. Golgi α-mannosidase II (GMII) has become a therapeutic target for drugs with anticancer activities. One critical task for successful application of GMII drugs in medical treatments is to decrease their unwanted co-inhibition of lysosomal α-mannosidase (LMan), a weakness of all known potent GMII inhibitors. A series of novel N-substituted polyhydroxypyrrolidines was synthesized and tested with modeled GH38 α-mannosidases from Drosophila melanogaster (GMIIb and LManII). The most potent structures inhibited GMIIb (Ki=50–76 μm, as determined by enzyme assays) with a significant selectivity index of IC50(LManII)/IC50(GMIIb) >100. These compounds also showed inhibitory activities in in vitro assays with cancer cell lines (leukemia, IC50=92–200 μm) and low cytotoxic activities in normal fibroblast cell lines (IC50>200 μm). In addition, they did not show any significant inhibitory activity toward GH47 Aspergillus saitoiα1,2-mannosidase. An appropriate stereo configuration of hydroxymethyl and benzyl functional groups on the pyrrolidine ring of the inhibitor may lead to an inhibitor with the required selectivity for the active site of a target α-mannosidase.

Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit na

Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-l-lyxitol (LIL). DIL showed potent [Ki/s