Synthesis of beta-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent.
Synthesis of beta-C-galacto-pyranosides with fluorine on the pseudoanomeric substituent.
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DOI：
10.1021/ol070169i
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发表时间：
2007-03
期刊：
影响因子：
5.2
通讯作者：
K. A. Tony;R. Denton;Anna Dilhas;J. Jiménez‐Barbero;D. Mootoo
中科院分区：
文献类型：
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作者：
K. A. Tony;R. Denton;Anna Dilhas;J. Jiménez‐Barbero;D. Mootoo
[反应：从中心1-硫代-1，2-O-异亚丙基缩醛醇和不同的α-氟代和α，α-二氟代酸开始，通过四步顺序制备用CHF和CF 2取代糖苷氧的β-C-半乳糖-吡喃糖苷。合成中的关键步骤是中间体烯醇醚-硫缩醛的氧代碳正离子环化为C1-取代的糖醛。
[reaction: see text] beta-C-galacto-Pyranosides with CHF and CF2 substitutes for the glycosidic oxygen were prepared through a four-step sequence starting from a central 1-thio-1,2-O-isopropylidene acetal alcohol and different alpha-fluoro- and alpha,alpha-difluoro acids. The key step in the synthesis is the oxocarbenium cyclization of an intermediate enol ether-thioacetal to a C1-substituted glycal.