Sugar synthesis trimethylsilyl triflate

Silylation, for instance, providing 1-0-trimethylsilyl glycosides frOTi 1-0-unprotected sugars in an anomerically pure form, has been shown by Tietze and coworicers to be useful in phenyl glycoside and l,l -diacetal (see Section 1.2.5) synthesis with 0-silylated acceptors and trimethylsilyl triflate as catalyst. The diastereoselectivity was dependent on 0-protection. 

A direct coupling reaction of cycloalkenylsilanes 329 with a silylated nucleobase 330 promoted by (diace-toxyiodo)benzene in the presence of trimethylsilyl triflate in dichloromethane at room temperature has been reported (Scheme 3.132) [385]. This procedure was applied in the synthesis of a novel carbocyclic cyti-dine derivative having bis(hydroxymethyl)cyclohexene as a pseudo-sugar moiety, which was designed as a potential anti-HIV agent. 

A synthesis of the pseudodisaccharide 3-0-methylsporaricin A has been reported, coupling suitably protected derivatives of the di-amino sugar 1-acetate and the diaminocyclitol using trimethylsilyl triflate, ... 

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