Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens
Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens
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DOI：
10.1016/j.carres.2007.05.019
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发表时间：
2007-08-13
影响因子：
3.1
通讯作者：
Du, Yuguo
中科院分区：
文献类型：
--
作者：
Cheng, Lijian;Chen, Qi;Du, Yuguo
采用“2+2”收敛策略合成了十二烷基4-O-乙酰基-α-L-吡喃鼠李糖基-（1 -> 3）-2，4-二-O-乙酰基-α-L-吡喃鼠李糖基-（1 -> 3）-4-O-乙酰基-α-L-吡喃鼠李糖基-（1 -> 4）-α-L-吡喃鼠李糖苷（cleistetroside-2）。异丙基1-硫代-α-L-吡喃鼠李糖苷（4）与4-O-乙酰基-2，3-O-异亚丙基-α-L-吡喃鼠李糖基三氯乙酰亚氨酸酯（8）和异丙基4-O-乙酰基-2，3-O-异亚丙基-α-L-吡喃鼠李糖基-（1 → 3）-2的顺序区域选择性3-O-糖基化，4-二-O-乙酰基-α-L-1-硫代-鼠李吡喃糖苷（10）与十二烷基4-O-乙酰基-α-L-吡喃鼠李糖基-（1 -> 4）-2，3-O-异亚丙基-α-L-吡喃鼠李糖苷（12），极大地促进了靶点的利用度。(c)2007爱思唯尔有限公司保留所有权利。
A tetrasaccharide, dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-alpha-L-rhamnopyranoside (cleistetroside-2), was synthesized via '2+2' convergent strategy. Sequential regioselective 3-O-glycosylation of isopropyl 1-thio-alpha-L-rhamnopyranoside (4) with 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl trichloroacetimidate (8), and isopropyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-1-thio-rh amnopyranoside (10) with dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-2,3-O-isopropylidene-alpha-L-rharnnopyranoside (12), greatly facilitate the target availability. (c) 2007 Elsevier Ltd. All rights reserved.