25546-57-0Relevant articles and documents
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Zervas
, p. 317 (1939)
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Efficient synthesis of nucleoside diphosphate glycopyranoses
Wendicke, Silke,Warnecke, Svenja,Meier, Chris
, p. 1500 - 1502 (2008/12/22)
(Chemical Equation Presented) Short and sweet: A new, short synthetic pathway for the synthesis of the enormously important class of nucleoside diphosphate sugars (NDP sugars) was developed using cyclo-saligenyl (cycloSal) nucleosyl phosphate triesters as
Glycosyl Imidates, 10. - Glycosyl Phosphates from Glycosyl Trichloroacetimidates
Schmidt, Richard R.,Stumpp, Michael
, p. 680 - 691 (2007/10/02)
The glycosyl trichloroacetimidates 1-α,β, 8-α, 11-α, 13-α, 15-α, and 17-α directly transfer the glycosyl moiety to phosphoric acid mono- and diesters.The acidity of the phosphoric acid derivatives used was sufficient for the activation of the trichloroacetimidates, therefore an additional acidic catalyst was not required.From the β-imidate 1-β α-glycosyl phosphate and from the α-imidates preferentially β-glycosyl phosphates were obtained.Reaction of dibenzyl phosphate (2a) and cetyl phosphate (2c) with 1-α demonstrated that β/α-anomerization iscatalyzed by traces of acid.The glycosyl phosphates 3a-α, 3a-β - 3c-β, 3f-α, 9a-β, and 9c-β were partly or totally deprotected.The structures of the synthezised compounds were assigned by 1H NMR spectroscopy and by comparison with literature data.
