Stereoselective synthesis of 1,2-13C2-L-fucose, 1,2-13C2-fucono-γ-lactone and 1,2-13C2-fucono-γ-lactol from non-sugar starting material
Stereoselective synthesis of 1,2-13C2-L-fucose, 1,2-13C2-fucono-γ-lactone and 1,2-13C2-fucono-γ-lactol from non-sugar starting material
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DOI：
10.1055/s-2005-917071
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发表时间：
2005-10-17
期刊：
影响因子：
2
通讯作者：
Ellames, GJ
中科院分区：
文献类型：
--
作者：
Gardiner, JM;Panchal, NR;Ellames, GJ
报道了一种从1制备L-岩藻糖和L-岩藻呋喃糖的有效合成方法。该路线旨在促进C1和/或C2处的C-13标记，并描述了C-13（2）-岩藻糖作为其四乙酸酯的合成。使用不对称二羟基化引入C2和C3立构中心，并控制由4的环化产生的内酯环尺寸以提供L-岩藻呋喃酮5，其结构通过衍生的三甲硅烷基醚6的X射线晶体分析明确确定。通过还原6然后脱保护产生岩藻糖内半缩醛7，然后提供L-岩藻糖，分离为其过乙酸酯8。
An efficient synthesis is reported for the preparation of L-fucose, and of L-fucofuranose, from 1. The route is designed to facilitate C-13 labelling at C1 and/or C2, and the synthesis of C-13(2)-fucose as its tetraacetate is described. The C2 and C3 stereocentres are introduced using asymmetric dihydroxylation, and the lactone ring size resulting from cyclisation of 4 was controlled to provide the L-fucofuranone 5, whose structure was unambiguously established by X-ray crystal analysis of the derived trisilyl ether 6. Generation of the fucose lactol 7 by reduction of 6 followed by deprotection then provided L-fucose, isolated as its peracetate 8.