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Claeyssens, F. Deleyn, E. Saman, and C. K. , 1975, 42, 352. Glycosides g7sbM 21 6 OTS CH2Cp H, COC H N2-p HO RO OH (18) (19) X (20) X = = OR S; R = Ac or Bz Se; R = Ac or Bz The use of l-thioglycosides in the synthesis of glycosyl halides is noted in Chapter 7. S%), suggesting that this reaction is thermodynamically controlled. 1*7 la6 l*’ M. L. Wolfrom and S. , 1975,41, 117. C. L. Bairnbridge, C. D. Mickey, and R. A. S. Perkin I, 1975, 1395. AHOH f-- t O, CMe2 H2C P O, CMe, O Ck, (23) Reagents: i, A; ii, Os0,-H,O,; iii, Me,CO-H+; iv, DBU; v, 08;vi, NaBH,; vii, NaIO,; viii, MeNHCH,CH,OH; ix, Ac,O-py ;x, H+; xi, Ph,P=CHCO,Et Scheme 11 R.
Butler, and B. Axelrod, Biochem. Biophys. Res. , 1974,60,635. A. L. Fink and K. J. Angelides, Biochem. Biophys. Res. , 1975,64, 701. R. Malinen and E. Sjostrom, Cellulose Chem. , 1975,9,231. 2 lo6 l06 20 Carbohydrate Chemistry In a study of the thermal properties of di- and tri-saccharides, it has been shown that the endothermic peak (given in parentheses) is characteristic of the glycosidic linkage; viz. (1 -+ 1)-linkages (265 "C), (1 -+ 4)-linkages (254 "C), (1 +. 121 S-Glycosides Interest in the use of thioglycosides as inhibitors and inducers of enzymes and for attachment to affinity-chromatography matrices continues.
1975,39,355. 82 Orthoester formation with acylated aldohexopyranosyl halides was accomplishedin the same way, but in the presence of silver trifluoromethanesulphonate. g. methyl 8a S. Hanessian and J. , 1975, 44, C14. 17 Glycosides AcO (16) 2,3,5-tri-O-benzoyl-/3-~-ribofuranoside and methyl 2,3,4,6-tetra-O-acetyl-/3-~glucopyranoside). 0° Treatment of /3-gentiobiose octa-acetate with antimony pentachloride has furnished, after acetylation, 6-O-/3-D-glucopyranosyl-a-~altropyranose octa-acetate, the reaction presumably involving a 3,4-acetoxonium 1,6-AnhydromaItosehas been transformed into 4-O-a-~-galactopyranosyl-+ -+ 83 84 86 89 OD *l N.