Iodoacetoxylation Reaction: A Convenient Route to α-Glycosides in the 2-Iodo and 2-Deoxy Series
作者:
Dominique Lafont,
Paul Boullanger,
Michael Rosenzweig,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 9
页码: 1377-1393
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002360
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Iodoacetoxylation of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (tri-O-acetyl-D-glucal) (1) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (di-O-acetyl-L-rhamnal) (3) gave the α-1,2-trans-1-O-acetyl-2-deoxy-2-iodo adducts with high stereoselectivities and good yields, in accordance with the results reported on 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1,5-an-hydro-2-deoxy-D-arabino-hex-1-enitol (hexa-O-acetyl lactal) (2). The α-1,2-transadducts were reacted with an excess of alcohol in the presence of trimethylsilyl trifluoromethane-sulfonate affording the corresponding α-1,2-trans-2-deoxy-2-iodo-glycopyranosides in good yields. The octyl 2-deoxy-2-iodo-α-D-glycosides10and11prepared in two steps from the glycals1and2were deiodinated and deacetylated, giving28and29, and the physicochemical-properties (cmc) of29are reported.
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