132430-67-2

Basic information

• Product Name: 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol
• CAS NO: 132430-67-2
• Molecular Weight: 590.716
• Mol File: 132430-67-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol(132430-67-2)
• EPA Substance Registry System: 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol(132430-67-2)

Safety Data

• Hazardous Substances Data: 132430-67-2(Hazardous Substances Data)

Upstream product

• 55726-19-7 2,3-O-Isopropylidene-5-O-trityl-D-ribofuranose 
• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 113571-56-5 (2S,3S,4S)-2,3-isopropylidenedioxy-4-trityloxymethyl-4-butanolide 
• 113626-56-5 (2S,3S,4S)-2,3-dihydroxy-4-trityloxymethyl-4-butanolide 
• 101758-68-3 (R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone 
• 84709-46-6 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 141410-49-3 (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 
• 132430-77-4 (R)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol 
• 132489-32-8 (S)-4-((3aS,4R,6aR)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-benzyloxy-butan-1-ol 
• 132430-76-3 (3aS,4R,6aR)-5-Benzyl-4-((R)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 132489-31-7 (3aS,4R,6aR)-5-Benzyl-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 113626-60-1 (2R,3S,4R)-N-benzyl-2-<(1S)-1-hydroxy-3-butenyl>-3,4-(isopropylidenedioxy)pyrrolidine 
• 113571-60-1 (2R,3S,4R)-N-benzyl-2-<(1R)-1-hydroxy-3-butenyl>-3,4-(isopropylidenedioxy)pyrrolidine 
• 132430-68-3 (2R,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-(trityloxymethyl)-pyrrolidine 
• 113571-58-7 (2R,3S,4R)-3,4-(isopropylidenedioxy)-2-(trityloxymethyl)-pyrrolidine 
• 132430-78-5 (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine 
• 113571-59-8 (2R,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol 
• 72741-87-8 swainsonine 

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.

Synthesis of (-)-swainsonine and (-)-8-epi-swainsonine from (S)- and (R)-glutamic acid derivatives

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