Hydrazinolysis of Sugar Sulfonates | Zendy

Tetsuo Suami | Zendy; Tadao Shoji | Zendy

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Hydrazinolysis of Sugar Sulfonates

Author(s) -

Tetsuo Suami,

Tadao Shoji

Publication year - 1970

Publication title -

bulletin of the chemical society of japan

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.145

H-Index - 99

eISSN - 1348-0634

pISSN - 0009-2673

DOI - 10.1246/bcsj.43.2948

Subject(s) - chemistry , acetylation , proton magnetic resonance , tosyl , sugar , medicinal chemistry , catalysis , organic chemistry , nuclear magnetic resonance , biochemistry , physics , gene

Hydrazinolysis of methyl 4,6-di-O-acetyl-2,3-di-O-tosyl-α-D-glucopyranoside (I) or methyl 2,6-di-O-benzoyl-3,4-di-O-mesyl-α-D-glucopyranoside (VI), followed by catalytic hydrogenation and acetylation, afforded methyl 2,4-diacetamido-3,6-di-O-acetyl-2,4-dideoxy-α-D-idopyranoside (II). Also methyl 2,3-di-O-acetyl-4,6-di-O-mesyl-α-D-glucopyranoside (VII) was treated analogously as described above to give methyl 4,6-diacetamido-2,3-di-O-acetyl-4,6-dideoxy-α-D-galactopyranoside (IX). The structures were studied by means of proton magnetic resonance spectra. And a reaction mechanism was also discussed.

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