methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-L-erythro-L-manno-nonoate | 116296-68-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-L-erythro-L-manno-nonoate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 116296-68-5
• 化学式: C₂₀H₂₉NO₁₂
• 分子量: 475.45
• InChiKey: VFEBRWKZQURCHT-DOQFWFFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-L-erythro-L-manno-nonoate 生成 (2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Bandgar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 492 - 494

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 乙酰氯 作用下， 以 乙醚 、 甲苯 为溶剂， -40.0~25.0 ℃ 、275.79 kPa 条件下， 反应 3.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-L-erythro-L-manno-nonoate
  参考文献：
  名称：

  Bandgar, Babasaheb P.; Hartmann, Michael; Schmid, Walther, Liebigs Annalen der Chemie, 1990, # 12, p. 1185 - 1195

  摘要：

  DOI：

文献信息

• An Expeditious Synthesis ofN-Acetylneuraminic Acid α-C-Glycosyl Derivatives (“α-C-Glycosides”) from the Anomeric Acetates
  作者：Adeline Malapelle、Anna Coslovi、Gilles Doisneau、Jean-Marie Beau

  DOI：10.1002/ejoc.200700181

  日期：2007.7

  efficiently with carbonyl compounds under Barbier conditions, providing a fast synthesis of C-ketosides. The α- and β-acetates are equally effective, and excellent yields are obtained for coupling with cyclic ketones. The procedure has been conveniently applied to the synthesis of a C-ketoside of N-acetylneuraminic acid with an attached linker, ready to use as a building block in the elaboration of

  在没有任何添加剂的情况下，通过二碘化钐对甲基 N-乙酰神经氨酸 3a 和 3b 的容易获得的全乙酰化衍生物进行还原金属化，生成相应的异头钐 (III) 有机金属化合物。这些中间体在 Barbier 条件下与羰基化合物有效反应，提供 C-酮苷的快速合成。α- 和 β- 乙酸酯同样有效，并且与环酮偶联可获得出色的产率。该程序已方便地应用于合成带有连接子的 N-乙酰神经氨酸的 C-酮苷，可随时用作构建多价生物探针的构建块。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of both epimeric 2-deoxy-n-acetylneuraminic acids and their behaviour towards CMP-sialate synthetase-a comparison with 2-β-methylketoside of n-acetylneuraminic acid
  作者：Walther Schmid、Rudolf Christian、Erich Zbiral

  DOI：10.1016/s0040-4039(00)82143-7

  日期：——

  tributyltin hydride to the corresponding 2-deoxy derivatives and , which gave after saponification the acids and . Both epimers are not inhibitors of CMP-sialate synthetase (EC 2.7.7.43), whereas the 2-β-methylketoside of Neu5Ac behaves as a competitive inhibitor of the activation of Neu5Ac (N-acetylneuraminic acid).

  甲基-2-β-氯-4,7,8,9-四-O-乙酰基-N-乙酰神经氨酸分别为1-2,3-二氢甲基-4,7,8,9-四-O-乙酰基-N -acetylneuraminate通过催化氢化或通过用还原氢化三丁基锡为相应的2-脱氧衍生物转化和，其皂化酸后，得到和。两种差向异构体都不是CMP-唾液酸合成酶的抑制剂（EC 2.7.7.43），而Neu5Ac的2-β-甲基酮苷充当Neu5Ac（N-乙酰神经氨酸）活化的竞争性抑制剂。
• Stereospecific synthesis of α-C-glycosyl derivatives (“α-C-glycosides”) of N-acetylneuraminic acid by samarium-mediated reductive desulfonylation of a glycosyl phenylsulfone
  作者：Yuguo Du、Robert J. Linhardt

  DOI：10.1016/s0008-6215(98)00054-8

  日期：1998.3

  Abstract A samarium-mediated Barbier reaction was performed to afford N -acetylneuraminic acid α - C -glycosyl compounds (“ α - C -glycosides”) in excellent yield. The neuraminic acid phenyl sulfone or 2-pyridyl sulfone derivatives reacted with ketones or aldehydes resulting in the instantaneous and stereospecific formation of Neu5Ac α - C -glycosides. The phenyl and the 2-pyridyl sulfone derivatives

  摘要进行了-介导的Barbier反应，以优异的收率得到了N-乙酰神经氨酸α-C-糖基化合物（“α-C-糖苷”）。神经氨酸苯基砜或2-吡啶基砜衍生物与酮或醛反应，导致瞬时和立体定向形成Neu5Acα-C-糖苷。苯基和2-吡啶基砜衍生物在该反应中同样有效。最后，该方法成功地用于制备C-二糖α-Neu5Ac-（2→6）Gal。
• HI/acetic acid reduction of peracetylated N-acetyl neuraminic acid esters to stereoselectively provide α-2-deoxy-2-hydrido derivatives
  作者：Jacquelyn Gervay、Travis Q. Gregar

  DOI：10.1016/s0040-4039(97)01323-3

  日期：1997.8

  acid were reacted with hydrogen iodide in acetic acid to stereoselectively provide α-2-deoxy-2-hydrido analogs. The reaction proceeds through formation of an anomeric iodide which, in the presence of excess HI, is reduced to give an enol intermediate. Kinetic protonation of the intermediate enol gives a 3.4:1 α:β mixture of 2-deoxy-2-hydrido derivatives. Under thermodynamic conditions the α-anomer

  使N-乙酰神经氨酸的全乙酰化酯衍生物与碘化氢在乙酸中反应，以立体选择性地提供α-2-脱氧-2-氢类似物。反应通过形成异头碘化物而进行，其在过量HI的存在下被还原以得到烯醇中间体。中间体烯醇的动力学质子化得到了2-脱氧-2-氢衍生物的3.4：1α：β混合物。在热力学条件下，仅形成α-异头物。
• Anomeric Acetates ofN-Acetylneuraminic Acid are UsefulC-Sialyl Donors in Samarium-Mediated Reformatsky Coupling Reactions
  作者：Adeline Malapelle、Zouleika Abdallah、Gilles Doisneau、Jean-Marie Beau

  DOI：10.1002/anie.200601209

  日期：2006.9.11