By Ward W Pigman; M L Wolfrom
ADVANCES IN CARBOHYDRATE CHEMISTRY VOL 1.
content material: entrance hide; 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 parts 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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C C . C . ~-Gliic~-~-ldooctose II O H H H H . C - C . C . C . C . CIIaOH D-G~UCO-L-~II~O- OH OH 11 OH OH OH - H O H O H H OHOH C . C . C C C C * CHO O H H H OIIH H 1 oc ti to1 D-Gala-L-gulooctose H O H O H H OHOH . C . c C . c . CHlOII D-Gala-L-gdooctitol (Identical OH H H OH €1 €I with A) H OHOHII OHH HOIIzC * C * C * c . C . C * C . C . C - H OHOHH OHH C * CHzOH D-GHla-L-ldO-OCtltO~ * C . tation can act as a guide in enabling the investigator to choose the path that leads to a final proof by one of Fischer’s conclusive methods.
Hudson, J . Am. Chem. ,64, 1612 (1942). R. hl. Hann, Alice T. Merrill and C. Hudson,J. Am. Chem. ,66, 1912 (1944). 22 C. 6. HUDSON amide and bcnzimidaeole confirmed this indication. The reduction of the pure crystalline lactone of this acid by sodium amalgam yielded a crystalline D-galaoctose, and the reduction of the pure sugar by hydrogen and Raney nickel in water led to a D-galaoctitol which is identical with D-a-glucooc titol; it shows the same crystalline form, meltisg point and rotation, and its octaacetate showecl m.
Richtmyer and Hudsonz0increased the yield of acetochloro-a-celtrobiose to 40-4570 by using a mixture of aluminum chloride and phosphorus pentachloride. The a- and 8-octaacetates exhibited a normal value for the rotation of the end carbon atom, A A ~ = +20,700. 6" in water; no mutarotation was observed. obtained, with [cY]D~O Acetylation of celtrobiose at a low temperature with acetic anhydride and pyridine furnished evidence that the crystalline sugar is a 8-form; the absence of mutarotation appears to indicate that the aqueous solution in equilibrium contains almost solely the 8-modification.
Advances in Carbohydrate Chemistry, 1 by Ward W Pigman; M L Wolfrom