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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Efficient synthesis of omega-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates
Teiichi Murakami1, Reiko Hirono, Yukari Sato
1Institute for Biological Resources and Functions, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan. t-murakami@aist.go.jp
Abstract:
Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C(8), C(12)) were investigated. ZnCl(2) was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl(4). The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters.
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