Deprotection trimethylsilyl trifluoromethanesulfonate

The seven-membered phostone 252 was synthesized by the reaction of methyl 2,3-di-0-benzyl-4,6-0-benzyl-idene-a((3)-D-glucopyranoside 251 with triethyl phosphate and trimethylsilyl trifluoromethanesulfonate. Protecting the acetal group of 251 interacted with triethyl phosphite and opened to give 252, which can be further selectively hydrolyzed or deprotected to give 253 or 254 <2003TL8797>. 

Recent improvements in the standard synthetic procedure using haloacetates have featured the use of trialkyi phosphites and activated acetates in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as activating reagent. " This reaction has proved to be of great value in constructing complex sugar phosphonates. For example, in the presence of TMSOTf, the Michaelis-Arbuzov reaction between protected ketose acetates and triethyl phosphite takes place in ( 1 FC F at room temperature to produce, after deprotection, the expected diethyl l-(methoxycarbonyl)alkyl-phosphonates in high yields. -" ... 

Soybean plants can produce the antibiotic phytoalexin when exposed to a fungal /1-glucan. A phytoalexin elicitor hexasaccharide was synthesized by automation using glycosyl phosphate building blocks (Scheme 7). The functionalized resin was submitted to building blocks in a five-fold excess with stoichiometric amounts of trimethylsilyl trifluoromethanesulfonate for 15 minutes at - 15 °C. The resin was washed and treated with hydrazine to affect the deprotection of the C6 hydroxyl. The sequence was repeated three times,... 

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