(2R,3R,4aR,5S,7S,8S,8aS)-7-Iodomethyl-2,3,5-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol | 226088-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4aR,5S,7S,8S,8aS)-7-Iodomethyl-2,3,5-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol
• 英文别名: (2R,3R,4aR,5S,7S,8S,8aS)-7-(iodomethyl)-2,3,5-trimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-8-ol
• CAS: 226088-93-3
• 化学式: C₁₃H₂₃IO₇
• 分子量: 418.226
• InChiKey: AAMOYERHGQIWGQ-IATRAZAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4aR,5S,7S,8S,8aS)-7-Iodomethyl-2,3,5-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol 在 2,6-二甲基吡啶 、 mercury(II) trifluoroacetate 、 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (2R,3R,4aS,5R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(6-iodo-benzo[1,3]dioxol-5-ylmethoxy)-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxin-6-ol
  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 、 alpha-甲基葡萄糖甙 在 camphor-10-sulfonic acid 、 咪唑 、 碘 、 三苯基膦 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 生成 (2R,3R,4aR,5S,7S,8S,8aS)-7-Iodomethyl-2,3,5-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol 、 (2R,3R,4aS,5S,7S,8R,8aR)-5-Iodomethyl-2,3,7-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol
  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