Pivalates in the selective protection and activation of maltose for the synthesis of sulfated 3-deoxy-maltosyl-(1 → 4)-α,α-trehalose

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• 作者：Wessel ; Hans Peter ; Trumtel ; Michel
• 关键词：Pivalates ; Deoxygenation ; 3-Deoxy-maltose ; Block glycoside synthesis ; Sulfates
• 刊名：Carbohydrate Research
• 出版年：1997
• 出版时间：January 2, 1997
• 年：1997
• 卷：297
• 期：2
• 页码：163-168
• 全文大小：524 K

文摘

Pivaloylation of maltose gave, in satisfactory yield, 1,2,6,2 32;,3 32;,4 32;,6 32;-hepta-O-pivaloyl-β-maltose which was converted to the 3-deoxygenated analogue in a Barton-McCombie reaction. This compound was used directly in a trimethylsilyl triflate-mediated glycosylation reaction with 2,3,6-tri-O-benzyl-α--glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α--glucopyranoside to give the corresponding maltosyl-(1 → 4)-α,α-trehalose derivative. After deprotection, the monodeoxygenated tetrasaccharide was sulfated; in the reaction product, one compound fully sulfated at the outer pyranose rings predominated. © 1997 Elsevier Science Ltd.