methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 142644-31-3

• 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 (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-4,5-diacetyloxy-2-methoxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 142644-31-3
• 化学式: C₂₁H₃₀O₁₄
• 分子量: 506.461
• InChiKey: XZJUGJXODDOJSY-YKFXCJJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  176.26
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 以100%的产率得到methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Studies on Sialic Acid. Part XXVII. Synthesis and Characterization of Furanose and Pyranose Derivatives of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).

  摘要：

  3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)的费舍尔甲基糖基化产物表明，KDN 的 α, β-呋喃糖和 α, β-吡喃糖之间存在着异构体平衡。尽管存在同分异构平衡，但用乙酸酐与吡啶对 KDN 及其衍生物进行过乙酰化反应只能得到 α 和 β-吡喃糖衍生物。获得的甲基苷和六-O-乙酰基衍生物通过 X 射线、核磁共振和立体二色光谱分析进行了表征。

  DOI：

  10.1248/cpb.40.879
• 作为产物：
  描述：

  甲醇 、 methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 反应 1.0h， 以6.17 g的产率得到methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER

  摘要：

  The synthesis of a range of C-9 substituted derivatives of the cc-methyl glycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thioacetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all prepared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 10 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy derivatives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.

  DOI：

  10.1081/car-100103960