76951-92-3

Basic information

• Product Name: 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose
• Synonyms: 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose
• CAS NO: 76951-92-3
• Molecular Weight: 423.463
• Mol File: 76951-92-3.mol

Chemical Properties

• CAS DataBase Reference: 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose(76951-92-3)
• EPA Substance Registry System: 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose(76951-92-3)

Safety Data

• Hazardous Substances Data: 76951-92-3(Hazardous Substances Data)

Upstream product

• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 501-53-1 benzyl chloroformate 
• 76951-85-4 6,7-(N-benzyloxycarbonyl)epimino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose 
• 76951-83-2 1,2:3,4-di-O-isopropylidene-6-O-(methylsulfonyl)-β-L-glycero-D-galacto-heptopyranurononitrile 
• 76951-84-3 (R)-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-aziridine 
• 19342-68-8 Hydroxy-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-acetonitrile 
• 161377-16-8 Benzyl-[(S)-2-(dimethyl-phenyl-silanyl)-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-amine 
• 161377-18-0 Benzyl-[(R)-2-hydroxy-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-carbamic acid benzyl ester 
• 28436-31-9 (R)-2-Amino-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanol 
• 83051-84-7 7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose 

Downstream Products

• 83051-87-0 [(R)-2-Hydroxy-1-((2R,3R,4S,5R)-3,4,5-trihydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid benzyl ester 

Relevant articles and documents

Stereocontrolled Hydroxymethylation of Carbohydrate Imines: Formal Synthesis of Destomic Acid and Lincosamine

Addition of magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose mediated by Ce(III)Cl3 or CuI/BF3*Et2O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford h

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.

SYNTHESIS OF DESTOMIC ACID AND ITS 6-EPIMER

The structure of 6-aminoheptonic acid component contained in destomycin A and C was confirmed first by chemical synthesis.