By M. L. (editor) Wolfrom
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Extra resources for Advances in Carbohydrate Chemistry, Vol. 13
Irvine and Hynd116J1s noted t h i t the methyl glycoside of D-glucosamine (methyl 2-amino-2-deoxy-~-glucopyranoside) is 100 times more resistant to acid hydrolysis than methyl a-mglucopyrunoside and remains essentially unchanged on heating at 100" with 5 % hydrochloric acid. Subsequently, Moggridge and Neuberger117 showed that this compound has a true glycosidic structure (XXXII) and that t,he unusual resistance toward acid hydrolysis is caused by the presence of the positively charged, amino group (-NH3*) which decreases the concentration of hydronium ions in the immediate vicinity of the glycosidic group.
Vaughsn, J. Chem. ,3367 40 F. SHAFIZADEH acetal derivatives. It appears that methyl 3 ,G-anhydro-2,4-di-O-methyl-aD-mannopyranoside is for the same reason hydrolyzed more rapidly than is the corresponding f u r a n o ~ i d e . 133This reaction provides good evidence for the cleavage of the cyclized bond in preference to that of the glycosidic group. The formation of an acyclic intermediate during the process of mutarotation was long ago postulated by Lowry,134-137 and has recently been confirmed by isotopic138and p o l a r o g r a p h i ~ ~investigations ~~-~~~ of aqueous solutions, and by kinetic studies with non-aqueous s o l ~ e n t s .
J . Heidt and C. B. Purves, J . Am. Chem. ,66, 1385 (1944). (87) E. A. Moelwyn-Hughes, Trans. ,26, 503 (1929). (88) C . B. Purves and C. S. Hudson, J . A m . Chem. , 69, 1170 (1937). (89) C. B. Purves, J . Am. Chem. ,66, 1969 (1934). 9 2. 4 5. 1 9. 5 46. 98 X lo-' min-I). The numbers represent the position OII which the substituent is axial. In the terminology suggested by Reeves, the normal chair conformat,ion is denoted by CZ for D sugars and 1C for L sugars. d Indirectly obtained value. 0 1,3,4 A2,5 p anomer 3.