(1R,2R,3S,4S,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane-5-ethanol | 1058108-16-9

• 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: (1R,2R,3S,4S,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane-5-ethanol
• 英文别名: 2-[(1R,2R,3S,4S,5R)-2,3,4-tris(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-5-yl]ethanol
• CAS: 1058108-16-9
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: DDGWDPPYEBIECA-MJXUZWQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1R,2R,3S,4S,5R)-5-allyl-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane 在 臭氧 、 sodium tetrahydroborate 、 三苯基膦 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 1.5h， 以95%的产率得到(1R,2R,3S,4S,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane-5-ethanol
  参考文献：
  名称：

  Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs

  摘要：

  A partially benzylated derivative of anhydro-D-altro-heptulose found in Coriaria japonica A, which is a synthetically useful unit, was successfully synthesized from a D-mannose derivative by a novel synthetic approach involving the intramolecular O-ketopyranosylation reaction developed by us. This synthetic approach was also applicable to the preparation of its four analogs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.068