Hydrazines inositol derivatives

Regioselective debenzoylation of nucleoside 2, 3 5-tri-O-benzoates using hydrazine hydrate has been reported. With 1 mol reagent in acetic acid-pyridine the 3 5-di-O-benzoyl derivative was produced when the bases were adenine, guanine, or indole, whereas with excess hydrazine hydrate in 1 1 chloroform-methanol, 98% of the 5-O-benzoyl derivative was produced (base = adenine or uracil). 3, 5-Di-O-benzoyl-2-deoxy-nucleosides gave a 90% yield of a 1 1 mixture of 3 - and 5-O-benzoyl nucleosides with 1 mol hydrazine hydrate in pyridine. Treatment of the mannose orthoacetate (5) with benzoyl chloride in pyridine gave 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl chloride and ethylbenzoate, whereas the related orthoester of mu co-inositol (6) gave 66% of the correspond-... 

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