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Extra info for Advances in Carbohydrate Chemistry and Biochemistry, Vol. 7
19) E. Sorkin and T. Reichstein, Helu. Chim. Acta, 28, 1 (1945); L. F. Wiggins, J . Chem. , 1590 (1949). (19a) Quite recently two additional heptuloses have been shown to form <2,6 > <2,7 > anhydrides in acid solution; bguloheptulose passes partially to 2,7-anhydro-j3-~-guloheptulopyranose [Laura C. Stewart, N. K. Richtmyer and C. S. Hudson, J . Am. Chem. ,74,2206 (1952)l and D-idoheptulose to 2,7-anhydrofl-D-idoheptulopyranose [J. W. Pratt, N. K. Richtmyer and C. S. , 74, 2210 (1952)l. (20) H.
Reeves, J . Am. Chem. ,71, 1737 (1949). (30) R. E. Reeves, J . Am. Chem. ,71, 2116 (1949). (31) R. E. Reeves, J . Am. Chem. ,72, 1499 (1850). 48 R. J. DIMLER hydroxyl bond angle of 60” in either case. Presumably the hydroxyl groups have to be closer together than in the 60” position for acetone to react. While the hydroxyl bond angle for the cis hydroxyls can be decreased to the necessary extent either by slight distortion of the ring or change of ring conformation, such is not possible for the trans hydroxyls.
Hann and C. S. Hudson, J . Am. Chem. , 68,2241 (1941). (6) G. ZemplBn, A. Ckrecs and T. , 78,676 (1940);A. Knauf, R. M. Hann and C. S. Hudson, J . Am. Chem. , 68, 1447 (1941). (7) R. J, Dimler, H. 4. Devb end G, E, Hilbert, J . Am, Chem. Soc,, 68,1377 (1946). A NEW CLASS OF HEXOSANS 39 D-glucosan < 1,4>/3 < 1,6> (1,6-anhydro-/3-~-glucofuranose) (11), as well as levoglucosan. A dextrorotatory D-galactosan first isolated by Hann and Hudson’ from the distillate from D-galactose was shown by Alexander, Dimler and Mehltretter* to be D-galactosan < 1,4 > a < 1,6> or 1,6-anhydro-a-D-galactofuranose (111).