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β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose

✍ Scribed by Luis F. Sala; Alicia Fernández Cirelli; Rosa M. de Lederkremer

Book ID
108308377
Publisher
Elsevier Science
Year
1980
Tongue
English
Weight
436 KB
Volume
78
Category
Article
ISSN
0008-6215

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2-Deoxy-P-D-lyxo-hexose (2-deoxy+-D-galactose, C,H,,O,), M, = 164.16, is monoclinic, P2, with a = 9.811(l), b = 6.953(l), c = 5.315(l) A, p = 91.58(2)", V = 362.5(l) A3, Z = 2, and D, = 1.504 g.cme3. The structure was solved by direct methods (MULTAN 79) and refined to R = 0.032 for 800 observed ref

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As part of a study of the effects of sugar analogs on glycoprotein biosynthesis'V2, it was necessary to prepare 3-deoxy-D-ribo-hexose (4) and 3-deoxy-D-arabino-hexose (5). Several satisfactory syntheses of these deoxy sugars have been reported3-7. For example, 3-deoxy-D-Cbo-hexose may be obtained by

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2-Deoxy-D-arabino-[6-13C]hexose (10), to be used to test the stability of 2-deoxy-D-arabino-hexose 6-phosphate in brain tissue, was prepared. 2-Deoxy-D-arabino-hexose was labeled at C-6 because of the large difference in chemical shift between C-6 in the free sugar and C-6 in the 6-phosphate. The sy