Formation of dihydrofuran derivatives by intramolecular substitution of the manno adducts formed by Michael reaction of a 1-O-acetyl-3-C-nitro-2-enopyranose derivative with 2,4-pentanedione and dibenzoylmethane

doi:10.1016/0008-6215(91)84050-O

Paper

Formation of dihydrofuran derivatives by intramolecular substitution of the manno adducts formed by Michael reaction of a 1-O-acetyl-3-C-nitro-2-enopyranose derivative with 2,4-pentanedione and dibenzoylmethane

Published Jun 10, 1991 · T. Sakakibara, A. Seta, T. Nakagawa

Carbohydrate Research

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Abstract

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Study Snapshot

Intramolecular substitution of manno adducts in Michael reaction leads to the formation of dihydrofuran derivatives, supported by similar reactions with dibenzoylmethane.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Formation of dihydrofuran derivatives by intramolecular substitution of the manno adducts formed by Michael reaction of a 1-O-acetyl-3-C-nitro-2-enopyranose derivative with 2,4-pentanedione and dibenzoylmethane

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References

Stereochemistry of Nucleophilic Addition Reactions. 10. Preparation of 2-C-Diacetylmethyl and 2-C-Acetylmethyl Derivatives with the Altro, Gluco, and Manno Configuration from Methyl 4,6-O-Benzylidene-2,3-dideoxy-3-nitro-α-D-erythro-hex-2-enopyranoside

The reaction of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro--D-erythro-hex-2-enopyranoside with acetylacetone in the presence of sodium hydroxide produces 2-C-diacetylmethyl and

Reaction of 1-O-acetyl-4,6-O-benzylidene-2,3-dideoxy-3-nitro-α-D-erythro-hex-2-enopyranose and its anomer with hydrazoic acid☆

Acetylation of glucopyranose leads to stable glucopyranose and less-stable mannopyranose, with solvent-effects affecting the reaction.

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