Methyl 3-azido-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside | 161128-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-azido-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside
• 英文别名: (1R,2R)-1-[(2R,3R,4S,6S)-4-azido-3-hydroxy-6-methoxy-6-(1,3-thiazol-2-yl)oxan-2-yl]propane-1,2,3-triol
• CAS: 161128-62-7
• 化学式: C₁₂H₁₈N₄O₆S
• 分子量: 346.364
• InChiKey: VQIQOVHNHQAONS-AGNBLMTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methyl 3-azido-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside 在 sodium tetrahydroborate 、 氨 、 lithium 、 sodium hydride 、 三氟甲烷磺酸甲酯 、 copper(II) oxide 、 copper dichloride 、 silver(l) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成
  参考文献：
  名称：

  Synthesis of a sialic acid analog with the acetamido group at C-4

  摘要：

  An isomer of N-acetylneuraminic acid (Neu5Ac) with the acetamido group at C-4 (iso-Neu4Ac) has been synthesized through stereoselective 1,4-conjugate addition of trimethylsilyl azide to a 2-thiazolyl alpha,beta-enone bearing a protected D-mannose moiety at C-beta. The same approach employing benzylamine as aminating reagent was less viable. In both routes the thiazole ring serves as a precursor to the formyl group which is oxidized to carboxylic acid in the final step of the synthesis.

  DOI：

  10.1016/s0957-4166(00)86296-5
• 作为产物：
  描述：

  (3SR,4R,5R,6S,7S)-3-Azido-8-O-tert-butyldiphenylsilyl-4,5,6,7,8-pentahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone 在 盐酸 、 甲醇 作用下， 反应 14.0h， 生成 Methyl 3-azido-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside
  参考文献：
  名称：

  Synthesis of a sialic acid analog with the acetamido group at C-4

  摘要：

  An isomer of N-acetylneuraminic acid (Neu5Ac) with the acetamido group at C-4 (iso-Neu4Ac) has been synthesized through stereoselective 1,4-conjugate addition of trimethylsilyl azide to a 2-thiazolyl alpha,beta-enone bearing a protected D-mannose moiety at C-beta. The same approach employing benzylamine as aminating reagent was less viable. In both routes the thiazole ring serves as a precursor to the formyl group which is oxidized to carboxylic acid in the final step of the synthesis.

  DOI：

  10.1016/s0957-4166(00)86296-5

文献信息

• Dondoni, Alessandro; Marra, Alberto; Boscarato, Alessia, Chemistry - A European Journal, 1999, vol. 5, # 12, p. 3562 - 3572
  作者：Dondoni, Alessandro、Marra, Alberto、Boscarato, Alessia

  DOI：——

  日期：——
• Synthesis of a sialic acid analog with the acetamido group at C-4
  作者：Alessandro Dondoni、Alessia Boscarato、Alberto Marra

  DOI：10.1016/s0957-4166(00)86296-5

  日期：1994.11

  An isomer of N-acetylneuraminic acid (Neu5Ac) with the acetamido group at C-4 (iso-Neu4Ac) has been synthesized through stereoselective 1,4-conjugate addition of trimethylsilyl azide to a 2-thiazolyl alpha,beta-enone bearing a protected D-mannose moiety at C-beta. The same approach employing benzylamine as aminating reagent was less viable. In both routes the thiazole ring serves as a precursor to the formyl group which is oxidized to carboxylic acid in the final step of the synthesis.