methyl 2,3-di-O-benzoyl-α-D-mannopyranoside | 149035-49-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-5-benzoyloxy-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl] benzoate
• CAS: 149035-49-4
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: DWMYGGCEIQZDIB-QKIGPUQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-α-D-mannopyranoside 在 吡啶 、 甲醇 、 硫酸 、 氨 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 [(2R,3R,4S,5S,6S)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-hydroxyoxan-4-yl] benzoate
  参考文献：
  名称：

  Concise syntheses of β-GlcNAcp-(1→6)-α-Manp-(1→6)-Manp and its dimer, and β-GlcNAcp-(1→2)-α-Manp-(1→6)-Manp

  摘要：

  beta-D-GlcNAcp-(1-->6)-alpha-D-Manp-(1-->6)-D-Manp and beta-D-GlcNAcp-(1-->2)-alpha-D-Manp-(1-->6)-D-Manp were synthesized as their methyl glycosides in a regio- and stereoselective way, whereas an ethylene glycol-coupled dimer of the former was prepared in a convergent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00570-6
• 作为产物：
  描述：

  methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 在 溶剂黄146 作用下， 生成 methyl 2,3-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Jansson, Per-Erik; Lindberg, Johan; Widmalm, Goeran, Acta Chemica Scandinavica, 1993, vol. 47, # 7, p. 711 - 715

  摘要：

  DOI：

文献信息

• Stereospecific β‐ <scp>l</scp> ‐Rhamnopyranosylation through an S _N i‐Type Mechanism by Using Organoboron Reagents
  作者：Nobuya Nishi、Kazuhiro Sueoka、Kiyoko Iijima、Ryuichi Sawa、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1002/anie.201808045

  日期：2018.10.15

  Stereospecific β‐l‐rhamnopyranosylations were conducted using a 1,2‐anhydro‐l‐rhamnopyranose donor and mono‐ol or diol acceptors in the presence of a glycosyl‐acceptor‐derived borinic or boronic ester. Reactions proceeded smoothly to provide the corresponding β‐l‐rhamnopyranosides (β‐l‐Rhap) with complete stereoselectivity in moderate to high yields without any further additives under mild conditions

  立体特异性β-升-rhamnopyranosylations使用1,2-脱水-进行升-rhamnopyranose供体和单醇或糖基-受体衍生的二取代硼酸或硼酸酯的存在下二醇受体。反应进行得很顺利，可以提供相应的β- 1-鼠李糖吡喃糖苷（β- 1- Rha p），在中等至高收率下具有完全的立体选择性，在温和条件下无需任何其他添加剂。使用13 C动力学同位素效应（KIE）测量和DFT计算的硼酸酯介导糖基化机理研究与一致的S N一致i机制具有爆炸的过渡状态。另外，本糖基化方法被成功地应用于三糖的合成，α-升-RHA p - （1,2）-β-升-RHA p - （1,4）-Glc p，衍生自肺炎链球菌血清型7B，7C和7D。
• Regioselective and 1,2-<i>cis</i>-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst
  作者：Akira Nakagawa、Masamichi Tanaka、Shun Hanamura、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1002/anie.201504182

  日期：2015.9.7

  Regioselective and 1,2‐cis‐α‐stereoselective glycosylations using 1α,2α‐anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl‐acceptor‐derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2‐cis‐α‐glycosides with high stereo‐ and regioselectivities in high yields without any further additives under mild reaction conditions. In addition

  在糖基受体衍生的硼酸酯催化剂存在下，使用1α，2α脱水糖基供体和二醇糖基受体进行区域选择性和1,2-顺-α-立体选择性糖基化反应。反应平稳进行，在温和的反应条件下，无需任何其他添加剂，即可高产率获得相应的具有高立体和区域选择性的1,2-顺-α-糖苷。另外，本糖基化方法已成功地应用于异黄酮糖苷的合成。
• Rhizobial saccharides 2. Selective synthesis of both diastereomers of 4,6-O-pyruvylated d-glycopyranosides
  作者：Thomas Ziegler

  DOI：10.1016/0040-4039(94)85023-2

  日期：1994.9

  Both diastereomers of 4,6-O-pyruvylated glycosides S- and R - 2 were selectively prepared from the corresponding 4,6-unprotected glycosides 1 by acetalation of the latter with methyl pyruvate and BF3-diethylether complex. In acetonitrile as the solvent, the thermodynamically favoured diastereomers having an axial-oriented methoxycarbonyl group are formed preferentially. In methyl pyruvate as the solvent

  的4,6-非对映体两者ø -pyruvylated苷小号和- [R - 2从相应的4,6-未受保护的糖苷选择性地制备1由后者的缩醛化用丙酮酸甲酯和BF 3 -diethylether复杂。在乙腈作为溶剂中，优先形成具有轴向取向的甲氧基羰基的热力学上有利的非对映异构体。在作为溶剂的丙酮酸甲酯中，具有赤道取向的甲氧基羰基的非对映异构体是主要产物，并且缩醛化的非对映选择性受起始糖苷1的2-O和3-O位置上的保护基的影响。
• Diastereoselective formation of pyruvylated glycosides from partly protected sugars and methyl pyruvate
  作者：Thomas Ziegler、Elisabeth Eckhardt、Gerhard Herold

  DOI：10.1016/s0040-4039(00)60097-7

  日期：1992.7

  Various partly protected sugars (gluco-, manno-, and galactopyranosides) were acetalized with methyl pyruvate in moderate to good yield with BF3-etherate as the condensing reagent. Thus, (1-methoxycarbonyl)ethylidene glycosides were obtained diastereoselectivity.

  各种部分受保护的糖（葡萄糖基，甘露糖苷和半乳糖吡喃糖苷）以丙酮酸甲酯缩醛化，并以BF 3-醚酸酯为缩合试剂。因此，获得了（1-甲氧基羰基）亚乙基糖苷的非对映选择性。
• Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75
  作者：Nobuya Nishi、Junki Nashida、Eisuke Kaji、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c7cc00269f

  日期：——

  A novel regio- and stereoselective [small beta]-mannosylation using 1,2-anhydromannose and a diol sugar acceptor in the presence of a boronic acid catalyst and its application are reported.

  报道了在硼酸催化剂存在下使用1，2-脱水甘露糖和二醇糖受体的新颖的区域和立体选择性β-甘露糖基化及​​其应用。