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Glycosyl imidates, 37. Direct O ‐glycosylation of compounds containing a PO(OH) moiety
Author(s) -
Eßwein Angelika,
Schmidt Richard R.
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880710
Subject(s) - chemistry , glycosyl , anomer , derivative (finance) , acetylation , moiety , phosphinate , glycosylation , phosphate , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , fire retardant , financial economics , economics , gene
The O ‐benzylated α and β‐glucosyl trichoroacetimidates 1a –α and 1a –β afforded with the phosphinic acid derivative 2 and the phosphonic acid derivative 3 directly the corresponding O ‐glucosylated products 4 and 5 , resp., with inversion at the anomeric center. The corresponding O ‐acetylated trichloroacetimidates 1b –α and 1b –β provided both the β‐products due to neighboring group participation. With the amidophosphoric acid derivative 6 and the trichloroacetimidate 1b –α the O ‐glucosylated compound 8 –β was obtained. The O ‐acetylated 6‐deoxy‐ L ‐talopyranosyl donor 12 behaved similarly. With compound 2 the α‐phosphinate 13 was formed. Dibenzyl phosphate gave the α‐phosphate 14 ; subsequent debenzylation led to the 6‐deoxy‐α‐ L ‐talopyranosyl phosphate 15 .