(1R,2R,6R,7S,8S,10S,11R)-10-Benzyloxy-8-methoxy-11-methoxymethoxy-3,9-dioxa-tricyclo[5.2.2.02,6]undecan-4-one | 137792-72-4

• 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,6R,7S,8S,10S,11R)-10-Benzyloxy-8-methoxy-11-methoxymethoxy-3,9-dioxa-tricyclo[5.2.2.02,6]undecan-4-one
• CAS: 137792-72-4；137792-73-5
• 化学式: C₁₉H₂₄O₇
• 分子量: 364.395
• InChiKey: MLENJFSGGMDFQO-WSQPWJPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (1R,2R,6R,7S,8S,10S,11R)-10-Benzyloxy-8-methoxy-11-methoxymethoxy-3,9-dioxa-tricyclo[5.2.2.02,6]undecan-4-one
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033