methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-talononate | 170453-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-talononate
• CAS: 170453-41-5
• 化学式: C₁₅H₂₅NO₈
• 分子量: 347.365
• InChiKey: ICZPJHOGULGHJT-PCEBWVJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.31
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  123.55
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-talononate 在 吡啶 、 sodium methylate 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 90.0h， 生成 N-[(1R,3R,4R,5R)-7-Oxo-3-((1R,2R)-1,2,3-trihydroxy-propyl)-2,6-dioxa-bicyclo[3.2.1]oct-4-yl]-acetamide
  参考文献：
  名称：

  Synthesis of 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid and 2,4-dideoxy-2-HeqN-acetylneuraminic acid

  摘要：

  We have continued our work to develop novel analogues of sialic acid [1-4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the glycerol side chain, N-acetyl group and the axially oriented carboxylic acid function [3]. In this report we describe the synthesis of two analogues, namely, 4-epi-2-deoxy-2-H-eq-N-acetylneuraminic acid (4-epi-2-d-2-H-eq-Neu5Ac) and 2,4-dideoxy-2-H-eq-N-acetylneuraminic acid (2,4-d(2)-2-H-eq-Neu5Ac).

  DOI：

  10.1016/0008-6215(95)00013-j
• 作为产物：
  描述：

  (2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 ruthenium(IV) oxide 、 硼烷铵络合物 、 potassium metaperiodate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.33h， 生成 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-D-talononate
  参考文献：
  名称：

  Synthesis of 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid and 2,4-dideoxy-2-HeqN-acetylneuraminic acid

  摘要：

  We have continued our work to develop novel analogues of sialic acid [1-4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the glycerol side chain, N-acetyl group and the axially oriented carboxylic acid function [3]. In this report we describe the synthesis of two analogues, namely, 4-epi-2-deoxy-2-H-eq-N-acetylneuraminic acid (4-epi-2-d-2-H-eq-Neu5Ac) and 2,4-dideoxy-2-H-eq-N-acetylneuraminic acid (2,4-d(2)-2-H-eq-Neu5Ac).

  DOI：

  10.1016/0008-6215(95)00013-j