177569-79-8

Upstream product

• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 100-46-9 benzylamine 
• 177493-29-7 5-O-(tert-butyldimethylsilyl)2,3-di-O-isopropylidene-D-ribitol 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 177493-30-0 5-O-(tert-butyldimethylsilyl)-1,4-bis(methanesulfonyl)-2,3-di-O-isopropylidene-D-ribitol 

Downstream Products

• 141410-49-3 (2S,3R,4S)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 
• 177493-31-1 (2S,3R,4S)-<1-Benzyl-3,4-(isopropylidenedioxy)pyrrolidin-2-yl>methyl methanesulfonate 
• 177493-32-2 (3R,4R,5S)-3-Azido-1-benzyl-4,5-(isopropylidenedioxy)piperidine 
• 176218-82-9 (2S,3R,4S)-2-azidomethyl-1-benzyl-3,4-(O-isopropylidene)dihydroxypyrrolidine 

Relevant academic research and scientific papers

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.

A divergent approach for the synthesis of some polyhydroxy pyrrolidines and piperidines from ribosylamine

A simple and efficient synthesis of 1,4-dideoxy-1,4-imino-d-ribitol, 1,4-dideoxy-1,4-imino-l-lyxitol, N-benzyl derivative of d-ribitol, 3,4,5-trihydroxy-piperidine, l-4-epi-isofagomine and d-3-epi-isofagomine, which are glycosidase inhibitors has been described from the commercially available d-ribose as a starting material.

Preparation of optically active 3-substituted piperidines via ring expansion: Synthesis of 4-amino- and 4-fluoro-1,4,5-trideoxy-1,5-imino-D-ribitol and 1,5-dideoxy-1,5-imino-D-ribitol

A new method for the preparation of optically active 3-substituted 1-benzylpiperidines based on the ring expansion of the 1-benzyl-2-(methylsulfonyloxymethyl)pyrrolidine 13 with various nucleophiles has been described. Synthesis of 4-amino-1,4,5-trideoxy-1,5-imino-D-ribitol 5, 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol 6 and 1,5-dideoxy-1,5-imino-D-ribitol 7 has also been achieved by a route which involves ring expansion of compound 13.