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

By M. L. (editor) Wolfrom

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A. Campbell and K. P. Link, J . B i d . , 122,635 (1938). (153) J. W. Green and E. Pacsu, J . A m . Chem. , 69, 2569 (1937). (154) J. Green and E. Pacsu, J . A m . Chem. , 60,2056, 2288 (1938). - 42 F. SHAFIZADEH derivatives from alditols, as discussed later (see page 60). 39 The feasibility of the steric requirements (suitable arrangement of C l to C4) for the formation of a five-membered ring in the xylo configuration is illustrated in Fig. 2 by the C2-C3 r o t a m e r ~ The . ~ ~ more stable, six-membered ring requires specific alignment and orientation of C5, as well as of the preceding carbon atoms.

Chem. ,620 (1940). A. B. Foster, W. G. Overend, M. Stacey and G. Vaughsn, J. Chem. ,3367 40 F. SHAFIZADEH acetal derivatives. It appears that methyl 3 ,G-anhydro-2,4-di-O-methyl-aD-mannopyranoside is for the same reason hydrolyzed more rapidly than is the corresponding f u r a n o ~ i d e . 133This reaction provides good evidence for the cleavage of the cyclized bond in preference to that of the glycosidic group. The formation of an acyclic intermediate during the process of mutarotation was long ago postulated by Lowry,134-137 and has recently been confirmed by isotopic138and p o l a r o g r a p h i ~ ~investigations ~~-~~~ of aqueous solutions, and by kinetic studies with non-aqueous s o l ~ e n t s .

9 X lo-' min-') under the above reaction conditions. b The numbers represent the position on which the substituent is axial. c In the terminology suggested by Reeves, the normal chair conformation is denoted by C1 for D sugars and 1C for L sugars. rings are strongly modified by the steric requirements of the second ring, so that a situation may arise in which a furanose structure is very definitely more stable arid less strained than the corresponding pyranose isomer. A well established instance is the behavior of the 3,6-anhydrohexosides, which is discussed later (see page 39).

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