3,4-di-O-benzoyl-5-O-chloroacetyl-1,2-O-isopropylidene-β-L-sorbopyranose | 368451-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-di-O-benzoyl-5-O-chloroacetyl-1,2-O-isopropylidene-β-L-sorbopyranose
• CAS: 368451-84-7
• 化学式: C₂₅H₂₅ClO₉
• 分子量: 504.921
• InChiKey: AMSYJDOLJKCORH-HOSCZWGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-5-O-chloroacetyl-1,2-O-isopropylidene-β-L-sorbopyranose 在 乙酸肼 作用下， 以 甲醇 为溶剂， 以65%的产率得到3,4-di-O-benzoyl-1,2-O-isopropylidene-β-L-sorbopyranose
  参考文献：
  名称：

  d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5

  摘要：

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00153-7
• 作为产物：
  描述：

  3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 在 吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 3,4-di-O-benzoyl-5-O-chloroacetyl-1,2-O-isopropylidene-β-L-sorbopyranose
  参考文献：
  名称：

  d-Fructose–l-sorbose interconversions. Access to 5-thio-d-fructose and interaction with the d-fructose transporter, GLUT5

  摘要：

  Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta -D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUTS, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00153-7