Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz(2)O or Piv(2)O.
Heating of non-substituted beta-D-glucopyranuronic acids in the presence of pivalic or benzoic anhydride in DMF gives 4-O-monoacylated or 2,4-di-O-acylated 6,3-lactones that can be easily transformed into corresponding methyl uronates bearing free OH-groups at C-2 and C-3 or C-3 only, respectively. This method was used for preparation of selectively 3-O-protected glucuronyl donors of thioglycoside and trichloracetimidate types.
Kornilov
A V
AV
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow B-334, Russia.
Sukhova
E V
EV
Nifantiev
N E
NE
D001565:Benzoates / Q000737:chemistry; D020723:Glucuronic Acid / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D010421:Pentanoic Acids / Q000737:chemistry
D001565:Benzoates; D007783:Lactones; D010421:Pentanoic Acids; C005566:pivalic acid; D020723:Glucuronic Acid; C102988:benzoic anhydride