By C.M. Rayner
This quantity is a testomony to the ongoing value of sulfur chemistry, and the super development that has been made lately.
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Extra resources for Advances in Sulfur Chemistry, Volume 2
With the exception of the thioglycosides and glycals, which require chemospecific activation and are routinely stable to functional group transformations, the other glycosyl donor reagents mentioned are inherently labile. glycosyl halide glycosyl trichloroacetimidate thioglycoside Figure 1. glycal glycosyl sulfoxide Iodine in Carbohydrate Chemistry 39 III. THIOGLYCOSIDES Chasing the "holy grail" of shelf-stable building blocks that might ultimately be compatible with a solid-phase glycosylation approach,^ we were particularly attracted to the thioglycosides.
Synthesis and Chemistry of Thioacylsilanes 5 a-(cis,trans) 15 An.. t. ,Ar H^ PH TBAF hr ''Ar P-form Scheme 19. "^^ The protiodesilylation of cycloadducts 12a, 13, and 14 presented some problems, because the initially formed H-substituted heterocycles underwent easy ring fragmentation (products 33 and 34) or aromatization (product 35)^° (Scheme 21). The decomposition products allowed the assignment of the regiochemistry of the cycloaddition. Fluoride-induced desilylation of silylated thiiranes 15 with tetraethyl ammonium fluoride (TEAF) resulted in a concomitant desilylation and desulfurization^^ (Scheme 22).
K. S. / Organomet. Chem. 1981, 208, 317. 73. S. Phosphorus Sulphur 1984, 21, 135. 74. ; Bonini, B. F ; Pedulli, G. F Tetrahedron Lett. 1987, 28, 3737. 75. ; Bonini, B. F ; Pedulli, G. F J. Chem. Soc, Faraday Trans. 1 1988, 84, 3347. 76. ; Stella, L. Ace Chem. Res. 1985,18, 917. 77. ; Bonini, B. F; PedulU, G. F Phys. Med 1989, 2-4, 151. 78. ; Vismara, E. Res. Chem. Intermed 1989,11, 117. 79. ; Pedulli, G. F ; Roffia, S. y. Org. Chem. 1997, 62, 6309. This Page Intentionally Left Blank IODINE, A VERSATILE REAGENT IN CARBOHYDRATE CHEMISTRY: ACTIVATION OF THIOGLYCOSIDES AND GLYCOSYL SULFOXIDES K.