65932-72-1Relevant academic research and scientific papers
SYNTHESE EN SERIE D-XYLOPYRANOSE: TRI-O-ACETYL-D-XYLOSES ET DERIVES CHLOROACETYLES
Utille, Jean-Pierre,Gagnaire, Didier
, p. 43 - 58 (1982)
Selective acetylation of D-xylose with acetic anhydride in dry pyridine at -30 deg C gave 1,2,3- and 1,2,4-tri-O-acetyl-α-D-xylopyranose with traces of 2,3,4-tri-O-acetyl-D-xylopyranose.Acetylation of D-xylose under conditions differing from the preceding ones only with respect to an azotropic distillation of an excess of pyridine before addition of acetic anhydride afforded a mixture of the eight possible triacetates.Unambiguous synthesis of 1,2,3-, 1,2,4-, and 1,3,4-tri-O-acetyl-β-D-xylopyranose was obtained from 3,4-di-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-xylopyranose, which also gave 1,3,4-tri-O-acetyl-α-D-xylopyranose.The aforementioned O-acetyl derivatives and the derived monochloroacetyl compounds were analyzed by 13C- and 1H-n.m.r. spectroscopy at 62.86 and 250 MHz, respectively.
