By Ward W Pigman; M L Wolfrom
ADVANCES IN CARBOHYDRATE CHEMISTRY VOL 1.
content material: entrance conceal; Advances in Carbohydrate Chemistry, quantity 1; Copyright web page; members to quantity I; Editors' Preface; Contents; bankruptcy 1. The Fischer Cyanohydrin Synthesis and the Configurations of Higher-carbon Sugars and Alcohols; bankruptcy 2. The Altrose team of drugs; bankruptcy three. Carbohydrate Orthoesters; bankruptcy four. Thio- and Seleno-Sugars; bankruptcy five. The Carbohydrate elements of the Cardiac Glycosides; bankruptcy 6. Metabolism of the Sugar Alcohols and Their Derivatives; bankruptcy 7. The Chemistry of the Nucleic Acids; bankruptcy eight. The Fractionation of Starch.
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Hudson, “The Fischer Cyanohydrin Synthesis and the Configurations of Higher-Carbon Sugars and Alcohols,” thk book, p. 1. 37 38 NELSON K. review of the sugars and their derivatives which have the altrose or a closely related configuration will include the aldohexoses waltrose and L-altrose, the ketohexoses D-allulose and L-allulose, and a ketoheptose, sedoheptulose; also two Bdesoxyaltroses and two naturally-occurring 2,6-didesoxyaltroses, digitoxose and cymarose; and finally the disaccharides neolactose and celtrobiose, which are 4-/3-~-galactopyranosido-D-dtrose and 4-~-D-ghcopyranosido-D-altroue, respectively.
XI. Cakiiirn D-Ahonate from D-&d&LCtoFR Itnd from Pectin. . . . . . XII. Compounds Possibly Related to Altrow XIII. Table I. D- and L-Altrose and Derivatives. . . . . . . . . . . . . . . XIV. Table 11. NeOlartOw. Celtmbiose. and Derivatives . . . . . . . . . . . 62 64 72 76 I. INTRODUCTION It was in 1910 that Levene and Jacobs’ first applied the classical cyanohydrin synthesis* to D-ribose (I), a five carbon atom aldehyde sugar (aldopentose) which had become more readily available through their earlier research on nucleic acids.
S. Hudson, J . Am. C h m . , 63, 1727 footnote 3 (1941). 17 R. C. Hockett and L. B. Chandler, J . Am. Chem. , 66, 627 (1944)have described a modification of this method of preparing D-altrose; cf. N. K. Richtmyer and C. , 62, 963 footnote 15 (1940). 18 N. K. Richtmyer and C. S. Hudson, J . Am. Chem. , 65, 740 (1943). 44 NELSON K. RICHTMYIR It is possible that the crystalline 8-D-altrose is a furanose form. Preliminary meaaurements of the extremely rapid change of rotation which occurs within the first three minutes after altrose is dissolved in water at 20" have indicated an initial highly negative rotation, although the extrapolated value [ ~ ] D ~ O - 69" is necessarily uncertain.
Advances in Carbohydrate Chemistry, 1 by Ward W Pigman; M L Wolfrom