methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-²H-D-glycero-D-galacto-non-2-enonate | 1158806-27-9

• 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-3-²H-D-glycero-D-galacto-non-2-enonate
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-5-deuterio-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1158806-27-9
• 化学式: C₂₀H₂₇NO₁₂
• 分子量: 474.426
• InChiKey: UZTLYEOULACYKZ-MLQCMUIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-3-²H-D-glycero-D-galacto-non-2-enonate 、 sodium acetate 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 1.0h， 生成 methyl [5-acetamido-2,4,7,8,9-penta-O-acetyl-3-(S)-bromo-3-²H-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranos]onate 、 methyl [5-acetamido-2,4,7,8,9-penta-O-acetyl-3-(R)-bromo-3-2H-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranos]onate
  参考文献：
  名称：

  Synthesis and Elimination of C-3-Labeled Thiosialosides

  摘要：

  The synthesis of C-3-labeled phenylthio sialic acid derivatives and an investigation of stereoselectivity in elimination reactions for the synthesis of 2,3-dehydro derivatives (glycals) is described. The experimental results are consistent with the existence of a conformational change and may be indicative of the intermediacy of an all-axial oxacarbenium ion.

  DOI：

  10.1021/ol500917k
• 作为产物：
  描述：

  在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-²H-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  Synthesis and Elimination of C-3-Labeled Thiosialosides

  摘要：

  The synthesis of C-3-labeled phenylthio sialic acid derivatives and an investigation of stereoselectivity in elimination reactions for the synthesis of 2,3-dehydro derivatives (glycals) is described. The experimental results are consistent with the existence of a conformational change and may be indicative of the intermediacy of an all-axial oxacarbenium ion.

  DOI：

  10.1021/ol500917k

文献信息

• Efficient Method for the Preparation of Peracetylated Neu5Ac2en by Flash Vacuum Pyrolysis
  作者：Evan J. Horn、Jacquelyn Gervay-Hague

  DOI：10.1021/jo900224t

  日期：2009.6.5

  Peracetylated Neu5Ac2en methyl ester, an intermediate in the synthesis of the influenza neuraminidase inhibitor Relenza, has been synthesized in high yields from peracetylated Neu5Ac methyl ester by flash vacuum pyrolysis. Mechanistic evidence including deuterium labeled studies and DFT (B3LYP) calculations suggest this transformation proceeds via an intramolecular syn-elimination.

  全乙酰化 Neu5Ac2en 甲酯是合成流感神经氨酸酶抑制剂 Relenza 的中间体，已通过快速真空热解从全乙酰化 Neu5Ac 甲酯以高产率合成。包括氘标记研究和 DFT (B3LYP) 计算在内的机械证据表明，这种转化是通过分子内同消除进行的。