methyl 4-O-benzoyl-6-bromo-3-O-propyl-6-deoxy-α-D-altropyranoside | 1178556-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-6-bromo-3-O-propyl-6-deoxy-α-D-altropyranoside
• CAS: 1178556-26-7
• 化学式: C₁₇H₂₃BrO₆
• 分子量: 403.27
• InChiKey: AXRUPYJNSGIHBS-NMNMXBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-6-bromo-3-O-propyl-6-deoxy-α-D-altropyranoside 在 水 、 sodium cyanoborohydride 、 锌 作用下， 以 丙醇 为溶剂， 以84%的产率得到(2R,3S,4R)-4-(benzoyloxy)-3-(propoxy)hex-5-en-1,2-diol
  参考文献：
  名称：

  Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1

  摘要：

  A new vitamin D-3 analogue, 2 alpha-propoxy-1 alpha, 25-dihydroxyvitamin D-3 (C3O1), was synthesized starting from D-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.032
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-O-propyl-α-D-altropyranoside 在 N-溴代丁二酰亚胺(NBS) 、 barium carbonate 作用下， 以 四氯化碳 为溶剂， 以73%的产率得到methyl 4-O-benzoyl-6-bromo-3-O-propyl-6-deoxy-α-D-altropyranoside
  参考文献：
  名称：

  Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1

  摘要：

  A new vitamin D-3 analogue, 2 alpha-propoxy-1 alpha, 25-dihydroxyvitamin D-3 (C3O1), was synthesized starting from D-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.032