83051-89-2

Upstream product

• 74-90-8 hydrogen cyanide 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 124-63-0 methanesulfonyl chloride 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 83093-79-2 (S)-2-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-aziridine 
• 83093-86-1 2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptono-1,5-lactone 
• 83093-80-5 methyl 2,3,4-tri-O-benzyl-6,7-(N-benzyloxycarbonyl)epimino-6,7-dideoxy-β-L-glycero-D-gluco-heptopyranoside 
• 83093-84-9 1,7-di-O-acetyl-2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-L-glycero-D-gluco-heptopyranose 
• 83113-47-7 methyl 7-O-acetyl-2,3,4-tri-O-benzyl-6-(N-benzyloxycarbonyl)amino-6-deoxy-β-L-glycero-D-gluco-heptopyranoside 
• 83093-94-1 methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside 

Relevant academic research and scientific papers

SYNTHESIS OF DESTOMIC AND epi-DESTOMIC ACID, AND THEIR C-6 EPIMERS

Four stereoisomers of 6-amino-6-deoxyheptonic acid, having the L-glycero-D-galacto (1), D-glycero-D-galacto (2), L-glycero-D-gluco (3), and D-glycero-D-gluco(4) configurations, were synthesized from D-galacto- (8) and D-gluco-dialdose (23) derivatives, respectively.Cyanomesylation of 8 and 23 gave two C-6 epimers, respectively, which were separately converted, via the corresponding 6,7-epimino derivatives, into 6-(benzyloxycarbonyl)amino-6-deoxy derivatives by reduction with lithium aluminium hydride, N-(benzyloxycarbonyl)ation, and acetolysis with acetic acid.After deprotection of each hemiacetal, the stereoisomers were oxidized with bromine, followed by total deprotection, to give 1-4.Among these products, 1 and 3 proved to be identical with the naturally occuring destomic and epi-destomic acid obtained from antibiotic destomycins.