A facile route to trans cyclic carbonates of sugars
作者： W.M. Doane , B.S. Shasha , E.I. Stout , C.R. Russell , C.E. Rist
DOI: 10.1016/S0008-6215(00)81835-2
关键词: Chemistry 、 Ethyl chloroformate 、 Pyridine 、 Reagent 、 Base (chemistry) 、 Medicinal chemistry 、 Organic chemistry 、 Vicinal 、 Triethylamine
摘要: Abstract Five-membered, cyclic carbonates are formed when vicinal trans -hydroxyl groups in D -glucopyranosides treated with ethyl chloroformate the presence of triethylamine. With these reagents, methyl 4,6- O -benzylidene-α- -glucopyranoside 2,3-carbonate ( 2 ), 2,6-di- -(methylsulfonyl)-α- 3,4-carbonate 5 and 4- -(ethoxycarbonyl)-6- -( p -tolylsulfonyl)-α- 8 ) were prepared. In contrast, pyridine is base present, only acyclic formed.
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