(3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate | 870543-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate
• 英文别名: (3S,4S,5R)-2-(2,2,2-trichloroacetyloxy)-5-azido-4-(benzyloxy)tetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate；4-azido-3-O-benzyl-4,6-dideoxy-2-O-levulinoyl-D-glucopyranosyl trichloroacetimidate；4-azido-3-O-benzyl-4,6-dideoxy-2-levulinoyl-D-glucopyranosyl trichloroacetimidate；4-azido-3-O-benzyl-6-desoxy-2-O-levulinoyl-α-D-glucopyranosyl trichloroacetamidate；[(3R,4S,5R,6R)-5-azido-6-methyl-4-phenylmethoxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 4-oxopentanoate
• CAS: 870543-35-4
• 化学式: C₂₀H₂₃Cl₃N₄O₆
• 分子量: 521.785
• InChiKey: KQVWASZVGATGCJ-OFSFNKJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate 、 (3S,4R,5R)-2-{(3S,4R,5R)-2-[(3R,4R,5S)-2-benzyloxytetrahydro-4,5-diacetoxy-6-methyl-2H-pyran-3-yloxy]tetrahydro-3,5-diacetoxy-6-methyl-2H-pyran-4-yloxy}tetrahydro-4-hydroxy-6-methyl-2H-pyran-3,5-diyl diacetate 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以90%的产率得到2-(2-(2-(2-(benzyloxy)tetrahydro-4,5-diacetoxy-6-methyl-2H-pyran-3-yloxy)tetrahydro-3,5-diacetoxy-6-methyl-2H-pyran-4-yloxy)-3,5-diacetoxytetrahydro-6-methyl-2H-pyran-4-yloxy)-5-azido-4-(benzyloxy)tetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate
  参考文献：
  名称：

  从头不对称合成炭疽四糖及相关四糖

  摘要：

  从乙酰呋喃已经开发出从天然产物炭疽四糖1和具有异头己基叠氮化物基团的类似物2的不对称方法。四糖的构建是通过传统的[3 +1]糖基化策略实现的。迭代非对映选择性钯催化糖基化，luche还原反应，非对映选择性二羟基化，选择性和区域选择性酰化物用于该组装升-鼠李糖-trisaccharide构建块。除Luche还原和二羟基化作用外，蒽酮构建基块还需要钯催化的叠氮化物烯丙基化和三氟甲磺酸酯转化来设定葡萄糖立体化学。

  DOI：

  10.1021/jo800691v
• 作为产物：
  描述：

  4-azido-3-O-benzyl-6-desoxy-2-O-levulinoyl-α-D-glucopyranoside 、 三氯乙腈 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以78%的产率得到(3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate
  参考文献：
  名称：

  WO2007/125089

  摘要：

  公开号：

文献信息

• Synthesis of a Spore Surface Pentasaccharide ofBacillus anthracis
  作者：Daniel B. Werz、Alexander Adibekian、Peter H. Seeberger

  DOI：10.1002/ejoc.200601082

  日期：2007.4

  An analogue 2 of the pentasaccharide 1 found on the spore surface protein BclA of Bacillus anthracis was synthesized by a (3+2) glycosylation approach. A robust building block for 3-linked α-rhamnose is presented. Benzoate groups were used to ensure α-selectivity for the rhamnose units. A radical-initiated reduction with tributyltin hydride was shown to be able to convert the NHTCA group into an acetylated

  在炭疽芽孢杆菌孢子表面蛋白 BclA 上发现的五糖 1 的类似物 2 是通过 (3+2) 糖基化方法合成的。提出了 3-linked α-rhamnose 的强大构建模块。苯甲酸酯基团用于确保鼠李糖单元的 α 选择性。用三丁基氢化锡进行自由基引发的还原被证明能够将 NHTCA 基团转化为乙酰化胺以及将叠氮基转化为游离胺。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Total Synthesis of AntigenBacillus Anthracis Tetrasaccharide—Creation of an Anthrax Vaccine Candidate
  作者：Daniel B. Werz、Peter H. Seeberger

  DOI：10.1002/anie.200502615

  日期：2005.10.7
• Molecular Analysis of Carbohydrate−Antibody Interactions: Case Study Using a <i>Bacillus anthracis</i> Tetrasaccharide
  作者：Matthias A. Oberli、Marco Tamborrini、Yu-Hsuan Tsai、Daniel B. Werz、Tim Horlacher、Alexander Adibekian、Dominik Gauss、Heiko M. Möller、Gerd Pluschke、Peter H. Seeberger

  DOI：10.1021/ja104027w

  日期：2010.8.4

  The process for selecting potent and effective carbohydrate antigens is not well-established. A combination of synthetic glycan microarray screening, surface plasmon resonance analysis, and saturation transfer difference NMR spectroscopy was used to dissect the antibody-binding surface of a carbohydrate antigen, revealing crucial binding elements with atomic-level detail. This analysis takes the first step toward uncovering the rules for structure-based design of carbohydrate antigens.
• De Novo Asymmetric Synthesis of the Anthrax Tetrasaccharide by a Palladium-Catalyzed Glycosylation Reaction
  作者：Haibing Guo、George A. O'Doherty

  DOI：10.1002/anie.200701354

  日期：2007.7.2