An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐D‐galactopyranose

doi:10.1081/CAR-120030468

Paper

An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐D‐galactopyranose

Published Dec 26, 2004 · Hong Liang, T. Grindley

Journal of Carbohydrate Chemistry

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Abstract

Abstract Methyl 2‐acetamido‐4‐amino‐2,4,6‐trideoxy‐α‐D‐galactopyranoside (10) was synthesized from D‐glucosamine hydrochloride in eight steps in an overall yield of 31%. Key steps include the selective benzoylation at O‐3 of methyl 2‐acetamido‐2,6‐dideoxy‐α‐D‐glucopyranoside in 89% yield and the subsequent Mitsunobu reaction using diphenylphosphoryl azide as the azide source which proceeded in 92% yield. Di‐ and mono‐benzyloxycarbonyl derivatives of 10 were also prepared. #Dedicated to Professor Gérard Descotes on the occasion of his 70th birthday.

Study Snapshot

Methyl 2acetamido4,4,6trideoxyDgalactopyranoside (10) was efficiently synthesized from D-glucosamine hydrochloride in eight steps, yielding 31% overall and di- and mono-benzyloxycarbonyl derivative

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

An Efficient Synthesis of Derivatives of 2‐Acetamido‐4‐amino‐2,4,6‐trideoxy‐D‐galactopyranose

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References

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