methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate | 132591-29-8

• 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-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate
• 英文别名: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-C-(2-propenyl)-D-erythro-β-L-gluco-nonulopyranosate；methyl (2S,3S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-hydroxy-3-prop-2-enyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 132591-29-8
• 化学式: C₂₃H₃₃NO₁₃
• 分子量: 531.514
• InChiKey: CPAUDUYBXPBFGM-YXGCQBTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  190
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate 在 吡啶 、 4-二甲氨基吡啶 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 80.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-3-C-(prop-2′-enyl)-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  An efficient synthesis of C3 C-alkylated Neu5Ac2en derivatives

  摘要：

  C3-modified Neu5Ac2en derivatives can be used to study the flexible 150-loop region of influenza virus sialidases and also provide a new template for the development of next-generation sialidase inhibitors. This Letter describes an efficient synthetic route towards the large scale synthesis of C3 C-alkylated Neu5Ac2en derivatives. The key intermediate, a 3-eq-allyl-Neu5Ac derivative, is formed by stereoselective addition of the allyl group in an equatorial configuration at C3, regardless of the stereochemistry of the bromohydrin precursor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.064
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S)-3-乙酰氨基-4-乙酰氧基-6-氯-6-(甲氧基羰基 在 disodium hydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 20.0~100.0 ℃ 、13.33 kPa 条件下， 反应 11.83h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-C-(prop-2'-enyl)-β-D-erythro-L-gluconon-2-ulopyranosonate
  参考文献：
  名称：

  An efficient synthesis of C3 C-alkylated Neu5Ac2en derivatives

  摘要：

  C3-modified Neu5Ac2en derivatives can be used to study the flexible 150-loop region of influenza virus sialidases and also provide a new template for the development of next-generation sialidase inhibitors. This Letter describes an efficient synthetic route towards the large scale synthesis of C3 C-alkylated Neu5Ac2en derivatives. The key intermediate, a 3-eq-allyl-Neu5Ac derivative, is formed by stereoselective addition of the allyl group in an equatorial configuration at C3, regardless of the stereochemistry of the bromohydrin precursor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.064

文献信息

• Paulsen, Hans; Matschulat, Peter, Liebigs Annalen der Chemie, 1991, # 5, p. 487 - 495
  作者：Paulsen, Hans、Matschulat, Peter

  DOI：——

  日期：——
• PAULSEN, HANS;MATSCHULAT, PETER, LIEBIGS ANN. CHEM.,(1991) N, C. 487-495
  作者：PAULSEN, HANS、MATSCHULAT, PETER

  DOI：——

  日期：——