2,3,4,6-Tetra-O-chloroacetyl-α-D-glucopyranose | 30572-07-7

• 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: 2,3,4,6-Tetra-O-chloroacetyl-α-D-glucopyranose
• 英文别名: 2,3,4,6-tetra-O-chloroacetyl-D-galctopyranose
• CAS: 30572-07-7；128948-99-2
• 化学式: C₁₄H₁₆Cl₄O₁₀
• 分子量: 486.087
• InChiKey: GZNCAPWJHANJFJ-VUOLPVENSA-N

物化性质

• 沸点：
  536.3±50.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-chloroacetyl-α-D-glucopyranose 在 乙醇 、 偶氮二甲酸二异丙酯 、 hydrazine dithiocarbonate 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 1-O-<5-(2,4-dichlorophenoxy)-2-nitrobenzoyl>-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of aryl d-gluco- and d-galacto-pyranosides and 1-O-acyl-d-gluco- and -d-gluco-pyranoses exploiting the mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction

  摘要：

  Glycosides (alpha- and beta-D-glucosides and -D-galactosides) derived from three pesticides, 2-tert-butyl-2,4-dinitrophenol,2,6-dibromo-4-cyanophenol, and 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, were synthesized from 2,3,4,6-tetra-O-chloroacetyl-D-gluco- and -D-galactopyranose by use of the Mitsunobu reaction. It was shown that selectivity for the beta-D anomer increases with the pK(a) of the acid component.

  DOI：

  10.1016/s0008-6215(00)90559-7
• 作为产物：
  描述：

  1,2,3,4,6-penta-O-chloroacetyl-β-D-glucopyranoside 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以80%的产率得到2,3,4,6-Tetra-O-chloroacetyl-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of aryl d-gluco- and d-galacto-pyranosides and 1-O-acyl-d-gluco- and -d-gluco-pyranoses exploiting the mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction

  摘要：

  Glycosides (alpha- and beta-D-glucosides and -D-galactosides) derived from three pesticides, 2-tert-butyl-2,4-dinitrophenol,2,6-dibromo-4-cyanophenol, and 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, were synthesized from 2,3,4,6-tetra-O-chloroacetyl-D-gluco- and -D-galactopyranose by use of the Mitsunobu reaction. It was shown that selectivity for the beta-D anomer increases with the pK(a) of the acid component.

  DOI：

  10.1016/s0008-6215(00)90559-7