Download Advances in Sulfur Chemistry, Volume 2 by C.M. Rayner PDF

By C.M. Rayner

ISBN-10: 0762306181

ISBN-13: 9780762306183

This quantity is a testomony to the ongoing value of sulfur chemistry, and the super growth that has been made in recent times.

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Si H R- ^ 18 ^R 36 Yields (%) R^ = H, CH3 Si = SiMea, SiMe2Ph R = Ar R = t-Bu 50-97 30 R = CH3, CycloalkyI Si 02 ^S02 ^Si Oxone R - ^ \ R 18 38 37 81-86% R^ = H, CH3 Si = SiMes, SiMeaPh R = CycloalkyI Scheme 23. CSF/CH3CN/H2O W-^S(0)n ^--^-^Ph 'S(0)n or CSF/DMSO/H2O SiMes 19n = 0 39n = 1 40 n = 2 Scheme 24. ^3X_3

Iodine in Carbohydrate Chemistry 41 thioglucoside to the corresponding glycosyl bromide on treatment with bromine (Fig. 4). However, neither Hiskey and Tucker nor Bonner comment on the reactivity of thioglycosides with iodine. It might have been expected that the less electrophilic iodine would be less likely than bromine to activate acetylated thioglycosides. The tetrahydropyranyl thioacetal is more reactive than a thioglycoside since it does not possess electron-withdrawing functionality. ^'* More recent studies have shown that iodine in conjunction with trityl perchlorate, which presumably forms iodonium perchlorate in situ, efficiently activates glycosyl dimethylphosphinothioates for glycosylation chemistry (Fig.

46 OMe BnO ll2,CAN,MeCN :ยง,Me BnO ^'^VcHiOBn I OMe BnO V--'^^^S BnO I MeOH BnOI uJttoOBn BnO BnO OMe Figure 13. -^^ An alternative activation system was therefore sought. B. Interhalogens It occurred to us that the interhalogens might serve as a more potent source of electrophilic iodine than I2 itself. The relative electrophilic character of such SPh ^ ^ * S P . * ^ PhS' \ PhS-SPh Figure 14. ^^ We have demonstrated that, in the absence of an acceptor alcohol, treatment of thioglycosides with I-Br gives rise to the corresponding glycosyl bromides in excellent yields.

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