Synthesis of 3,4,6-Tri-O-methyl-D-glucose, -D-galactose, and -D-mannose

Synthesis of 3,4,6-Tri-O-methyl-D-glucose, -D-galactose, and -D-mannose

Reaction of 1,3,4,6-tetra-O-acetyl- D -glucose, - D -mannose, and - D -galactose with dihydropyran and p-toluenesulfonic acid in dichloromethane gave the corresponding 2-tetrahydropyranyl ethers. Deacetylation, methylation, and hydrolysis gave 3,4,6-tri-O-methyl- D -glucose, 3,4,6-tri-O-methyl- D -m...

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Veröffentlicht in:Canadian journal of chemistry 1974-01, Vol.52 (2), p.291-292
Hauptverfasser: Berry, Joffre M, Choy, Yuen-Min, Dutton, Guy G. S
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container_title Canadian journal of chemistry
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creator Berry, Joffre M
Choy, Yuen-Min
Dutton, Guy G. S
description Reaction of 1,3,4,6-tetra-O-acetyl- D -glucose, - D -mannose, and - D -galactose with dihydropyran and p-toluenesulfonic acid in dichloromethane gave the corresponding 2-tetrahydropyranyl ethers. Deacetylation, methylation, and hydrolysis gave 3,4,6-tri-O-methyl- D -glucose, 3,4,6-tri-O-methyl- D -mannose, and 3,4,6-tri-O-methyl- D -galactose in 60, 28, and 25% overall yields, respectively. A small amount of 3,5,6-tri-O-methyl- D -galactose was also obtained.
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title Synthesis of 3,4,6-Tri-O-methyl-D-glucose, -D-galactose, and -D-mannose
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