Development of ketoside-type analogues of trehalose by using α-stereoselective O-glycosidation of ketose
Development of ketoside-type analogues of trehalose by using α-stereoselective O-glycosidation of ketose
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DOI：
10.1002/ejoc.200700145
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发表时间：
2007-08-01
影响因子：
2.8
通讯作者：
Ikegami, Shiro
中科院分区：
文献类型：
--
作者：
Namme, Rie;Mitsugi, Takashi;Ikegami, Shiro
本文报道了海藻糖酮甙类类似物的立体选择性合成。在三甲基甲硅烷基三氟甲磺酸酯的促进下，庚-2-吡喃葡萄糖与三甲基甲硅烷基α-吡喃糖苷的O-糖苷化仅得到α-吡喃酮基α-吡喃醛糖苷。α-酮吡喃糖基β-醛吡喃糖苷和α-酮吡喃糖基α-酮吡喃糖苷也以类似的方式合成。通过氢解除去羟基部分的苄基保护基团，得到完全脱保护的海藻糖类似物。((c)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2007）。
The stereoselective synthesis of ketoside-type analogues of trehalose is described. O-Glycosidation of hept-2-ulopyranose with trimethylsilyl alpha-pyranoside promoted by trimethylsilyl trifluoromethanesulfonate afforded alpha-ketopyranosyl alpha-aldopyranosides exclusively. alpha-Ketopyranosyl beta-aldooyranosides and a-ketopyranosyl alpha-ketopyranosides were also synthesized in a similar manner. The benzyl protecting groups of the hydroxy moieties were removed by hydrogenolysis to afford fully deprotected trehalose analogues. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).