By C.M. Rayner
This quantity is a testomony to the continued significance of sulfur chemistry, and the great development that has been made lately.
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Extra resources for Advances in Sulfur Chemistry, Volume 2
We assume that the P-glycoside is the kinetic product and that it undergoes an acid-catalyzed epimerization in situ. It is conceivable that H-I is responsible for effecting this process (see also Fig. 8 and Section X). Attempts to glycosylate Boc-protected serine were very disappointing. This is perhaps not surprising since glycosylation reactions tend to be acidic. ^^ VIII. ACTIVATION OF "DISARMED" THIOGLYCOSIDES Perhaps the principal cost in solution-phase oligosaccharide synthesis is manpower, related to the routine but laborious need for chromatography after each round of glycoside coupling.
While many of the traditional glycosylation procedures have been explored for the synthesis of glycoamino acid building blocks, few methods give uniformly reliable results. ^^ Glycosylation with acetobromogalactose gives the expected |3-glycoside in nearquantitative yield. Glycosylation of the same acceptor with an "armed" thiogalactoside, however, is less straightforward. In the absence of an acid scavenger, such as potassium carbonate, the thermodynamically favored a-glycoside is formed. In K.
RAVINDRANATHAN KARTHAet al. 40 CH2OAC CHjOAc AcO AcO' Br Figure 4. l2 + TrtC104 ^ P 30? © e ^= CHjOBn f BnO-*''T^ *OR RC)H BnOi + Trt I CHzOBn BnO-^-^^V BnO 1 Me' Me Figure 5. Ph-I0 + Tf20 )Tf. TfO ^ ROH ^ 'R - r ^R Ph A ^ Ar-IFj O N ^ ^ © "AT I AT Figure 6. 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.
Advances in Sulfur Chemistry, Volume 2 by C.M. Rayner