Revisiting the armed-disarmed concept rationale:: S-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis
Revisiting the armed-disarmed concept rationale:: S-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis
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DOI：
10.1021/ol050969y
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发表时间：
2005-07-21
期刊：
影响因子：
5.2
通讯作者：
Demchenko, AV
中科院分区：
文献类型：
--
作者：
Kamat, MN;Demchenko, AV
已经发现，2-O-苄基-3,4,6-三-O-酰基SBox糖苷的反应性甚至比“解除武装”的全酰化衍生物要低得多。这一发现已应用于各种寡糖的合成，其单体单元通过顺式-顺式、反式-顺式和顺式-反式顺序糖苷键连接。武装（苄基化）供体对中度（解除）武装（酰化）以及随后过度解除武装（2-O-苄基-3,4-O-二酰化）受体的两阶段激活也被证明是可行的。
It has been discovered that 2-O-benzyl-3,4,6-tri-O-acyl SBox glycosides are significantly less reactive than even "disarmed" peracylated derivatives. This finding has been applied to the synthesis of various oligosaccharides, the monomeric units of which are connected via cis-cis, trans-cis, and cis-trans sequential glycosidic linkages. Two-stage activation of the armed (benzylated) donor over moderately (dis)armed (acylated) and, subsequently, over disarmed (2-O-benzyl-3,4-O-diacylated) acceptor has also proven to be feasible.