(2R,3R,4aR,5S,8S,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3,5-trimethoxy-2,3-dimethyl-7-methylene-hexahydro-pyrano[3,4-b][1,4]dioxine | 226088-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2R,3R,4aR,5S,8S,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3,5-trimethoxy-2,3-dimethyl-7-methylene-hexahydro-pyrano[3,4-b][1,4]dioxine
• 英文别名: (2R,3R,4aR,5S,8S,8aS)-8-[(6-iodo-1,3-benzodioxol-5-yl)methoxy]-2,3,5-trimethoxy-2,3-dimethyl-7-methylidene-4a,5,8,8a-tetrahydropyrano[3,4-b][1,4]dioxine
• CAS: 226088-78-4
• 化学式: C₂₁H₂₇IO₉
• 分子量: 550.344
• InChiKey: CPWAEYAAFDKASQ-JRBOJVLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aR,5S,8S,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3,5-trimethoxy-2,3-dimethyl-7-methylene-hexahydro-pyrano[3,4-b][1,4]dioxine 在 2,6-二甲基吡啶 、 mercury(II) trifluoroacetate 作用下， 以 水 、 丙酮 为溶剂， 生成 (2R,3R,4aR,5S,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(6-iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-benzo[1,4]dioxin-6-one
  参考文献：
  名称：

  An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

  摘要：

  In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00334-2
• 作为产物：
  描述：

  2,2,3,3-四甲氧基丁烷 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4aR,5S,8S,8aS)-8-(6-Iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3,5-trimethoxy-2,3-dimethyl-7-methylene-hexahydro-pyrano[3,4-b][1,4]dioxine
  参考文献：
  名称：

  An approach to (+)-pancratistatin from D-glucose: A conformational lock solves a stereochemical problem

  摘要：

  In previous work we discovered that reductive Pd-mediated aryl-enone cyclization of an advanced intermediate resulted in epimerization of a critical stereocenter. Analysis of conformational and steric effects could rationalize the result. Based on that analysis it was anticipated that a conformational lock could suppress the undesired epimerization. Results reported herein confirm that expectation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00334-2