Carbohydrate Chem, Monosaccharides, disaccharides and by Royal Society of Chemistry (Great Britain)

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UCQ-COmpOUndSare produced from those with aD-manno-stereochemistry and vice versa. l5 (- 0 (3) (4) Reagents: i, ROH, b a s e Scheme 3 a- Di-Q-alkylphosphorodithioc acids add to peracetylated glycals to give high yields of predominantly 2-deoxy-a-D-qlycosyl (6) adducts. g. can be obtained (Scheme , ) . I 6 Further in the area of glycosides 0 CH~OAC AcO A ,ji-&,,,, GMe CH~OAC -L--+ AcO 2H 2H R c x u ~ ~ . n c,(NeO),P(S)SH, b W , Ndt'l~,McOc(,u, Ac20-Py (6) Scheme 4 of deoxysugars, methyl 2,6-dideoxy-a-D-arabIno * -hexopyranoside can be made readily from 2,6-dibromo-2,6-dideoxy-a-D-mannopyranosyl bromide by methanolysis followed ~y reductive debromination (Chapter 12).

S ( m ~Abstl;, . 1988, 6816). C b , 1988, 669. Schmidt,J . Carbohydr. Chem.. 1988, 1, 435. Kumazawa, J . Am. (:hem. , 1988, JJ&, 7910. Kamikawa, Tetrahedron Lett,, 1988, 29, 1189. Riess,Tetrahedron Lett,, 1988, 2193. , 1988, 1op, 55 090). Yang, w e XuebaQ, 1988, G ,239 (Chem. , 1988, 190 679). Bioore. W&, 1987, 654 ( ! b D . Abst: . L , 1988, 167 810). McElhaney,Chem. Phys. m, 1987, Q, 113 (Chem. @, 187 121). , 110 794). Siemsen, Can. J. C h m , 1988, 187. Warrener, Tetrahedron, 1988, 44, 4591.

It was then converted to (80) which has previously been converted to shodomycin, and a new synthesis of this antibiotic was therefore claimed. l*s SsPh Reage&: i , PhScCL;O, E t j N H20; iiL, MCPBA HopH Scheme 25 Compounds ( 8 4 ) (tentative identification) and ( 8 5 ) , which can also be classified as a ketose and a racemic cyclitol OR OH OH CH20H (84) R = p-D-Gal-p C@:a. lq7 In the area of aryl C-furanosides it has been shown that 0furanosides with a dimethyl(g-to1yl)silyl ether group at p-2, on g-tolyl ctreatment with tin (IV) chloride, give 1,2-&-related glycofuranosides.

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