Enamines derived from 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose and β-dicarbonyl compounds. A synthesis of 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose

doi:10.1016/S0008-6215(00)80340-7

Paper

Enamines derived from 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose and β-dicarbonyl compounds. A synthesis of 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose

Published Jun 1, 1971 · A.Gómez Sánchez, A. C. Ventulá, U. Scheidegger

Carbohydrate Research

Q2 SJR score

6

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0

Influential Citations

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Abstract

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Study Snapshot

Enamines 12-15 were successfully synthesized by treating 3,4,6-tri-O-acetyl-2-amino-2-deoxy--D-glucopyranose with barium methoxide, yielding various products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Enamines derived from 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose and β-dicarbonyl compounds. A synthesis of 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose

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References

Enamines derived from 2-amino-2-deoxy-D-glucose and acetoacetic esters.

Enamines are intermediates in the formation of pyrroles from 2-amino sugars and -dicarbonyl compounds.

Reactions of glycosylamines with β-diketones and with benzoylacetaldehyde

Glycosylamines from common aldohexoses react with -diketones and benzoylacetaldehyde to produce N-glycosyl derivatives of -amino,-unsaturated ketones.

Reactions of 2-amino-2-deoxy-D-glucose with benzoylacet-aldehyde and 1-phenyl-1,3-butanedione

This study demonstrates the potential of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-[1-(3-oxo-3-phenyl-1-propenyl)amino]--D -glucopyranose hydrochloride for the

Reaction between 2-amino-2-deoxy-D-glucose and 2,4-pentanedione

2-amino-2-deoxy-D-glucose and 2,4-pentanedione react in neutral solution to produce 3-acetyl-2-methyl-5-(D-arabino-tetrahydroxybutyl)pyrrole (I), which may serve as a

Citations

Molybdenum(VI)cis-dioxo complexes bearing sugar derived chiral Schiff-base ligands: synthesis, characterization, and catalytic applications

Molybdenum(VI)-cis-dioxo complexes bearing sugar-derived chiral Schiff-base ligands show high catalytic activity for epoxidation and moderate enantiomeric induction, with potential applications in epoxidation and enantio

A novel regio- and highly stereoselective anomeric deacetylation of 2-aminosugar derivatives

Silica gel-mediated anomeric deacetylation of 2-aminosugar derivatives in methanol offers a mild, inexpensive method for selective deprotection of carbohydrate templates with high stereoselectivity and minimal by-products.

Regioselective Benzoylation of N-Protected D-Glucosamine

Regioselective benzoylation of N-protected D-glucosamine yields various derivatives, with fully benzoylated compound 6 being the major product when excess benzoyl chloride is used.

Protection of the amino group of amino sugars by the acylvinyl group: Part I, glycoside formation by the fischer reaction

The Fischer reaction effectively prepares glycosides from 2-deoxy-2-[(2,2-dimethoxycarbonylvinyl)amino]--d-glucopyranoside, with the 2,2-diacylvinyl group removed selectively under non-acidic conditions.

Reaction of ethyl 2-amino-4,6-O-benzylidene-2-deoxy-d-gluconate with acetylenic esters

Ethyl 2-amino-4,6-O-benzylidene-2-deoxy-d-gluconate reacts with acetylenic esters to produce sugar enaminones, with methyl propiolate, ethyl phenylpropio