A New Glucose: Towards Conformationally Locked Hexoses through Annulation
A New Glucose: Towards Conformationally Locked Hexoses through Annulation
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一种新的葡萄糖：通过成环实现构象锁定的己糖
DOI：
10.1002/ejoc.200500031
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发表时间：
2005
影响因子：
2.8
通讯作者：
S. Ramesh
中科院分区：
文献类型：
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作者：
G. Mehta;S. Ramesh
借助碳环的成环作用，开发了一类新的表面修饰的碳水化合物，它们具有锁定的、富含轴向的构象和双极性面结构。这些新的反式-十氢化萘为基础的碳水化合物已经合成，从简单的芳香族前体，如四氢化萘，通过臭氧分解的适当保护的烯丙醇，然后通过级联的分子内缩醛化，以产生糖吡喃部分。从常见的环状反式环己二烯二醇（trans-CHD）前体立体选择性合成（外消旋）环己烷环状0-吡喃葡萄糖苷和α-呋喃葡萄糖苷强调了我们方法的多功能性。已通过合成两种区域异构的环状古洛糖衍生物证明了成环策略在产生碳水化合物多样性中的功效，所述两种区域异构的环状古洛糖衍生物仅在糖部分上的成环位点上不同。新糖的MLP表面和固态结构的映射表明，环烷烃成环导致糖亲水性的表面改性和微调。（C Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2005）。
A new family of surf ace-modified carbohydrates with locked, axial-rich conformations and bipolarofacial architectures has been developed with the aid of carbocyclic ring annulation. These novel trans-decalin-based carbohydrates have been synthesized, from simple aromatic precursors such as tetralin, through the ozonolysis of an appropriately protected allylic alcohol, followed by a cascade of intramolecular acetalizations to generate the sugar pyran moiety. The stereoselective synthesis of (racemic) cyclohexane-annulated 0-glucopyranoside and a-glucofuranoside from a common annulated trans-cyclohexadiene diol (trans-CHD) precursor under-scores the versatility of our approach. The efficacy of the annulation stratagem in generating carbohydrate diversity has been demonstrated through the synthesis of two regioisomeric annulated gulose derivatives, which differ only in the site of ring annulation on the sugar moiety. The mapping of the MLP surface and solid-state architecture of the new sugar shows that cycloalkane annulation results in surface modification and fine-tuning of sugar hydrophilicity. (C Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
S.Kawamura、H.Yamakoshi 和 M.Nojima：“4,4-二甲基-2-环己烯-1-基乙酸酯和 4,4-二甲基-2-环戊烯-1-基乙酸酯的臭氧分解。空间立体之间的竞争
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