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Download PDF by M. L. (editor) Wolfrom: Advances in Carbohydrate Chemistry, Vol. 13

By M. L. (editor) Wolfrom

ISBN-10: 0120072130

ISBN-13: 9780120072132

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Extra resources for Advances in Carbohydrate Chemistry, Vol. 13

Example text

Roy. (London), 74, 188 (1904). 4 530 140 150 25 H HO m HHO H 104(~&-l) HO HO OMe H OMe H XXI Methyl 8-D-galactopyranoside Methyl a-u-galactopyranoside OH -O@OH - C3 H XXII H XXI). The results indicated a considerable variation arising from differences in the configuration a t C4 (as well as of those of the glycosidic centers). More extensive investigations by Riiber and S@rensena2 and by Isbell (82) C. N. Itiiber and N . A. S@rensen,Kgl. Norske Videnskab. Selskabs Skrifter, No. 1, 1 (1938); Chem.

9, 1 (1954). (157) R. U. Lemieux and C. Brice, Can. J . , 33, 109 (1955); 34, 1006 (1956). (158) R. U. Lemieux, C. Brice and G. Huber, Can. J . , 33, 134 (1955). (159) 1’. Brewster, F. Hiron, E. D. Hughes, C. K. Ingold and P. A. D. S. Rao, Nature, 166, 170 (1950); C. K. Ingold, “Structure and Mechanism in Organic Chemistry,’’ G. , London, 1953, p. 396. 44 F. sHAFIZADEH this decomposes to a carbonium ion, which affords an alcohol of predominantly inverted configuration plus some olefins. The reaction proceeds through the SN1mechanism, and complete racemization is prevented by a masking effect of the departing group.

5. Hudson, J. Am. Chem. ,69, 1124 (1937). (134) T. M. Lowry, J. Chem. ,83, 1314 (1903); 86,1551 (1904). (135) G. F. Smith and T. M. Lowry, J. Chem. , 665 (1929). (136) T. M. Lowry, J. Chem. ,127, 1371 (1925). (137) H. Hudson, M. L. Wolfrom and T. M. Lowry, J. Chem. ,1179 (1933). (138) K. Goto and T. Titani, Bull. Chem. Japan, 16, 403 (1941). (139) S. M. Cantor and Q. P. Peniston, J. Am. Chem. , 62,2113 (1940). (140) J. M. Los, L. B. Simpson and K. Wiesner, J . A m . Chem. , 78,1564 (1956). (141) W.

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Advances in Carbohydrate Chemistry, Vol. 13 by M. L. (editor) Wolfrom


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