76951-85-4

Upstream product

• 501-53-1 benzyl chloroformate 
• 76951-84-3 (S)-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 
• 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 
• 76951-83-2 1,2:3,4-di-O-isopropylidene-6-O-(methylsulfonyl)-β-L-glycero-D-galacto-heptopyranurononitrile 
• 76951-82-1 1,2:3,4-di-O-isopropylidene-6-O-(methylsulfonyl)-α-D-glycero-D-galacto-heptopyranurononitrile 
• 152554-12-6 1,2:3,4-Di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranose 6,7-sulfate 
• 152554-11-5 (3aR,5S,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 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 
• 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 
• 152574-30-6 7-Deoxy-1,2:3,4-di-O-isopropylidene-7-(phenyldimethylsilyl)-D-glycero-α-D-galacto-heptopyranose 
• 59401-69-3 1,2:3,4-di-O-isopropylidene-D/L-glycero-α-D-galacto-hepto-1,5-pyranose 

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 
• 83051-87-0 [(S)-2-Hydroxy-1-((2R,3R,4S,5R)-3,4,5-trihydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-carbamic acid benzyl ester 
• 76951-87-6 1,2:3,4-di-O-isopropylidene-6--6-deoxy-L-glycero-α-D-galacto-heptopyranose 
• 76951-92-3 6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose 
• 83051-84-7 7-O-acetyl-6-(benzyloxycarbonyl)amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose 
• 83051-83-6 1,2:3,4-Di-O-isopropylidene-6-N-((carbobenzyloxy)amino)-6-deoxy-7-O-acetyl-L-glycero-α-D-galacto-heptopyranose 

Relevant academic research and scientific papers

Use of (chloromethyl)dimethylphenylsilane in sugar chemistry. Stereo-controlled approach to destomic acid and 1-deoxy-nojirimycin

Addition of magnesium chloride (1d) to 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose, and further processing of the resulting anti-α-hydroxy-silane adduct by a well-established sequence of reactions, gives a precursor to destomic acid 2.Similarly, addition of the Grignard reagent 1d to 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose proceeds with a high degree of stereoselectivity to give, after further elaboration of the syn-α-hydroxy-silane adduct, the antibiotic 1-deoxynojirimycin.

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.