Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2-octulosonic acid derivatives
Stereoselective synthesis of oligo-α(2,8)-3-deoxy-D-manno-2-octulosonic acid derivatives
复制标题
DOI：
10.1002/anie.200503299
复制
发表时间：
2006-01-01
影响因子：
16.6
通讯作者：
Takahashi, T
中科院分区：
文献类型：
--
作者：
Tanaka, H;Takahashi, D;Takahashi, T
（化学反应式）糖与无环糖前体的碘烷氧基化（见方案）导致二-和三-α（2，8）-3-脱氧-D-甘露-2-辛酮糖酸（KDO;见图片）的有效立体选择性合成。糖形成α-连接的3-碘-KDO衍生物。吡喃环的开环提高了C8羟基的反应性。NIS= N-碘代琥珀酰亚胺，Tf=三氟甲磺酸酯，MS=分子筛。
(Chemical Equation Presented) Iodoalkoxylation (see scheme) of a glycal with an acyclic saccharide precursor leads to an efficient stereoselective synthesis of di-and tri-α (2, 8)-3-deoxy-D-manno-2-octulosonic acid (KDO; see picture). The glycal forms α-linked 3-iodo-KDO derivatives. The opening of the pyran ring improves the reactivity of the C8 hydroxy group. NIS= N-iodosuccimide, Tf= triflate, MS= molecular sieves.