First Synthesis of 2,3,4-Tri-O-benzyl-5-thio-d-ribono-1,5-lactone

doi:10.1055/S-2005-872079

Paper

First Synthesis of 2,3,4-Tri-O-benzyl-5-thio-d-ribono-1,5-lactone

Published Jul 20, 2005 · Ludovic Chaveriat, I. Stasik, J. Lalot

Synthesis

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Abstract

The first synthesis of 2,3,4-tri-O-benzyl-5-thio-D-ribono-1,5-lactone was achieved, in five steps, from 5-bromo-5-deoxy-D-ribono-1,4-lactone; displacement of the bromide group, in methyl 2,3,4-tri-O-benzyl-5-bromo-5-deoxy-D-ribonate (7), gave methyl 2,3,4-tri-O-benzyl-5-S-acetyl-5-thio-D-ribonate (10) in 96%. yield. Saponification of compound 10 gave the methyl 2,3,4-tri-O-benzyl-5-thio-D-ribonic acid (11) in 98% yield. Treatment of 11 with DIC-HOBt as coupling reagents led, after cyclisation, the target compound, 2,3.4-tri-O-benzyl-5-thio-D-ribono-1,5-lactone (12) in 75% yield.

Study Snapshot

This study demonstrates a novel method for synthesizing 2,3,4-tri-O-benzyl-5-thio-D-ribono-1,5-lactone from 5-bromo-5-deoxy-D-ribono-1,4-lactone in a five-step process.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

First Synthesis of 2,3,4-Tri-O-benzyl-5-thio-d-ribono-1,5-lactone

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References

Citations

Synthesis of 1-hydroxybenzotriazoles angularly annulated by furazan or furoxan rings

This study demonstrates the successful synthesis of 6-hydroxy-6H-[1,2,3]triazolo[4,5-e][2,1,3]benzoxadiazole and its isomeric isomers using 2,4-dinitrosoresorcinol as a starting material.