The Introduction of the Diphenylhydrazino Substituent by Triflate Displacement. Photochemical Synthesis of an Aminodeoxy Sugar
作者:
ThomasW. Flechtner,
Helen Pohlid,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1984)
卷期:
Volume 3,
issue 1
页码: 107-116
ISSN:0732-8303
年代: 1984
DOI:10.1080/07328308408057900
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
The reaction of 1,2:3,4-di-O-isopropylidene-6-O-triflyl-α-d-galactopyranose (4) with N, N-diphenyl-hydrazine in boiling benzene produced 6-deoxy-1,2:3,4-di-O-isopropylidene-6-(N', N'-diphenylhydrazino)-α-d-galactopyranose (2). The Pyrex-filtered irradiation of2in distilled 2-propanol produced 6-amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose (5) and carbazole. The results obtained show that, while this procedure is a feasible route for aminodeoxy sugar synthesis, product yields are too low for this synthesis to be of general value.
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