1,2,3,4,6-penta-O-chloroacetyl-β-D-glucopyranoside | 128902-67-0

• 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: 1,2,3,4,6-penta-O-chloroacetyl-β-D-glucopyranoside
• 英文别名: 1,2,3,4,6-Penta-O-chloroacetyl-α-D-mannopyranose；1,2,3,4,6-Penta-O-chloroacetyl-α-D-glucopyranose；1,2,3,4,6-Penta-O-chloroacetyl-α-D-galactopyranose；1,2,3,4,6-penta-O-chloroacetyl-α,β-D-galactopyranose
• CAS: 128902-67-0；128902-69-2；128902-73-8；141990-44-5；141990-45-6
• 化学式: C₁₆H₁₇Cl₅O₁₁
• 分子量: 562.569
• InChiKey: AMPORDCCVYGWRN-MYJHBCJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-chloroacetyl-β-D-glucopyranoside 在 偶氮二甲酸二异丙酯 、 乙酸肼 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 2-tert-butyl-4,6-dinitrophenyl 2,3,4,6-tetra-O-chloroacetyl-β-D-galactopyranoside
  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：

  D-吡喃葡萄糖 、 氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以96.5%的产率得到1,2,3,4,6-penta-O-chloroacetyl-β-D-glucopyranoside
  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