27299-03-2Relevant articles and documents
Hydroxy group acidities of partially protected glycopyranosides
Matwiejuk, Martin,Thiem, Joachim
, p. 2180 - 2187 (2012/06/30)
A comprehensive acidity study of carbohydrate hydroxy groups has been carried out. Relative acidities (Ke) were determined spectrophotometrically for partially methylated methyl α-D- glycopyranosides. Apparently, the acidity is strongly affected by intramolecular hydrogen bonding as well as stereochemistry and solvation. By comparison with pKe and pKa values of aliphatic alcohols and polyols the first estimation of the pKa values for partially protected glycopyranosides was obtained. These findings contribute to the understanding of the relative reactivities of carbohydrate hydroxy groups.
A convenient method for the preparation of all of the partially methylated derivatives of methyl α-D-mannopyranoside and α-D-galactopyranoside
Mega, Tomohiro,Nishikawa, Atsushi,Ikenaka, Tokuji
, p. 313 - 319 (2007/10/02)
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SYNTHESIS OF METHYL DERIVATIVES OF URONIC ACIDS. II. SYNTHESIS OF THE 2,3-, 2,4-, AND 2,4-DI- AND 2,3,4-TRI-O-MEETHYL ETHERS OF METHYL (METHYL α-D-GALACTOPYRANOSID)URONATE
Grishkovets, V. I.,Zemlyakov, A. E.,Chirva, V. Ya.
, p. 259 - 261 (2007/10/02)
Unidirectional methods are proposed for the synthesis of the 2,3-, 2,4-, and 3,4-di-, and 2,3,4-tri-O-methyl ethers of methyl (methyl α-D-galactopyranosid)uronate by the oxidation (CrO3-H2SO4-acetone) of the corresponding methyl O-benzyl-O-methyl-α-D-galactopyranosides having unsubstituted 6-OH groups to the corresponding (methyl O-benzyl-O-methyl-α-D-galactosid)uronic acids followed by the esterification with CH2N2 and catalytic hydrogenolysis of the benzyl groups.