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By M. L. (editor) Wolfrom

ISBN-10: 0120072130

ISBN-13: 9780120072132

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Pitzer, in “Steric Effects in Organic Chemistry,” M. S. , New York, N. , 1956, p. 1. (78) H. C. Brown, J . Chem. ,1248 (1956); Abstracts Papers A m . Chem. S O C . , 132, 3D (1957). (79) W. Klyne, in “Progress in Stereochemistry,” W. , Butterworths Scientific Publications, London, 1954, Vol. 1, p. 72. 26 F. SHAFIZhDEH cause of (a) the distortion of the tetrahedral valency angle or (b) the presence of eclipsed bonds; whereas the strain in the well-staggered, chair conformation of six-membered rings originates from the non-bonded interactions of the axial groups.

The results of these investigations (see Table 111) indicate that the same relationship also holds for the methylated glycosides, although the latter compounds appear to be generally more stable. I n the aldopyranoside series, extensive data are available on the rates of hydrolysis of a large variety of methyl glycosides. The systematic work on this subject was initiated by E. F. 81 He compared the rates of hydrolysis of anomeric pairs of methyl D-glucopyranosides (XVIII and XIX) and methyl D-galactopyranosides (XX and (80) F.

Ij'rom these data, it also appears that the stabilizing effect of the hydroxyl group at C2 is independent of the (106) (1933). (107) (108) (109) (110) (111) (112) R. P:iul, Bull. SOC. chinz. France, [5] 1, 971 (1934); Compt. , 197, 1652 M. Bergmmn, H. Schotte and W. , 66, 158 (1922). M. , 443, 223 (1925). M. Bergniann and W. , 470, 38 (1929). F. Shufizudeh and M. Chem. , 4612 (1957). W. G. Overend, M. Stacey and J. StanBk, J. Cheni. ,2841 (1949). G. N . Itichurds, Chern. & Ind. (London), 228 (1955).

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

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