Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars

Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars
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DOI:
10.1016/j.tetlet.2005.03.016
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发表时间:
2005-04-25
影响因子:
1.8
通讯作者:
Ikegami, S
Ikegami, S
中科院分区:
化学4区
文献类型:
--
作者:
Namme, R;Mitsugi, T;Ikegami, S

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酸促进的1-外亚甲基糖的α-立体选择性O-糖苷化反应成功地应用于PI-88类似物的合成。以甲磺酸为促进剂,对甲氧基苄基保护的1 ′-C-甲基-α-二糖得到高产率。选择性脱保护和糖苷化的顺序有效地提供1-C-甲基-五糖。(c)2005爱思唯尔有限公司保留所有权利。
Acid-promoted alpha-stereoselective O-glycosidation of 1-exo-methylenesugars was successfully applied to the synthesis of a PI-88 analogue. By using methanesulfonic acid as a promoter, 1'-C-methyl-alpha-disaccharides with p-methoxybenzyl protection were obtained in high yield. The sequence of selective deprotection and glycosidation provided 1-C-methyl-pentasaccharide efficiently. (c) 2005 Elsevier Ltd. All rights reserved.