318239-79-1

Upstream product

• 62983-44-2 6-bromo-6-deoxy-(S)-ascorbic acid 
• 99663-50-0 2,3-O,O-dibenzyl-6-O-tosyl-L-ascorbic acid 
• 104040-10-0 6-bromo-2,3-O,O-dibenzyl-L-ascorbic acid 

Downstream Products

• 918419-44-0 6'-((2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-L-arabinitol)-4-N-yl)-2',3'-di-O-benzyl-6'-deoxy-L-ascorbic acid 
• 918419-48-4 6'-((2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabinitol)-4-N-yl)-2',3'-di-O-benzyl-6'-deoxy-L-ascorbic acid 
• 918419-44-0 6'-((2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-L-arabitinol)-4-N-yl)-2',3'-di-O-benzyl-6'-deoxy-L-ascorbic acid 
• 918419-48-4 6'-((2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabitinol)-4-N-yl)-2',3'-di-O-benzyl-6'-deoxy-L-ascorbic acid 
• 1313583-60-6 4-amino-1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-1H-[1,3,5]triazin-2-one 
• 1313583-68-4 2-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-2H-[1,2,4]triazine-3,5-dione 
• 1313583-72-0 1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-[1,3,5]triazinane-2,4,6-trione 
• 1313583-59-3 N-{1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 1380084-15-0 1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl]-1H-1,2,4-triazole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME

The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

Crystal structures, circular dichroism spectra and absolute configurations of some L-ascorbic acid derivatives

Chiral 2,3-O,O-dibenzyl ethers of L-ascorbic acid with 4-(5,6-epoxy)- (4) and 6-O-tosyl- (8) functional groups were studied by X-ray crystallography and circular dichroism (CD) spectroscopy. The stereostructure of 2,3-O,O-dibenzyl-5,6-isopropylidene-L-ascorbic acid (6) and 8 was determined by X-ray crystal structure analysis. Comparison of the CD-spectra of 4 and 8 with the CD-spectra of their synthetic precursors (2-3, 5-7) and L-ascorbic acid (1) itself, as well as crystal structures of 6 and 8 permitted to deduce the absolute configuration of 4. Thus, the chiral atoms C-4 and C-5 in 4 have R and S configurations, which is consistent with the configuration of 1.

Synthesis and antitumor activities of novel pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid and 4,5-didehydro-5,6-dideoxy-L-ascorbic acid

The new pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid (8-10) were synthesized by condensation of uracil and its 5-fluoro- and 5-trifluoromethyl-substituted derivatives with 4-(5,6-epoxypropyl)-2,3-O,O-dibenzyl-L-ascorbic acid (7), whi