145259-99-0Relevant academic research and scientific papers
Rhizobial saccharides. 2. Selective synthesis of both diastereomers of 4,6-O-pyruvylated D-glycopyranosides
Ziegler
, p. 6857 - 6860 (2007/10/02)
Both diastereomers of 4,6-O-pyruvylated glycosides S- and R-2 were selectively prepared from the corresponding 4,6-unprotected glycosides 1 by acetalation of the latter with methyl pyruvate and BF3-diethylether complex. In acetonitrile as the solvent, the thermodynamically favoured diastereomers having an axial-oriented methoxycarbonyl group are formed preferentially. In methyl pyruvate as the solvent, the diastereomers having an equatorial-oriented methoxycarbonyl group are the main products and the diastereoselectivity of the acetalation is influenced by the protecting groups at positions 2-O and 3-O of the starting glycosides 1.
Convenient synthesis of 4,6-O-pyruvate acetal containing glycosides via tetraisopropyldisiloxanediyl protected sugars
Ziegler,Eckhardt,Neumann,Birault
, p. 1013 - 1017 (2007/10/02)
Treatment of alkyl D-glycopyranosides and alkyl or phenyl 1-thio-β-D-glycopyranosides 1 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gave the corresponding 4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) protected glycosides 2 which were subsequen
Diastereoselective formation of pyruvylated glycosides from partly protected sugars and methyl pyruvate
Ziegler,Eckhardt,Herold
, p. 4413 - 4416 (2007/10/02)
Various partly protected sugars (gluco-, manno-, and galactopyranosides) were acetalized with methyl pyruvate in moderate to good yield with BF3-etherate as the condensing reagent. Thus, (1-methoxycarbonyl)ethylidene glycosides were obtained di
