(4aR,6S,7R,8aS)-6-Hydroxymethyl-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol | 476687-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6S,7R,8aS)-6-Hydroxymethyl-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• 英文别名: (4aR,6S,7R,8aS)-6-(hydroxymethyl)-2,2,4a-trimethyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 476687-87-3
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: LPJVAAUPOCCREB-UYAYMFIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,6S,7R,8aS)-6-Hydroxymethyl-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (4aR,6S,7R,8aS)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.

  DOI：

  10.1021/ol026804w
• 作为产物：
  描述：

  (2S,4aS,6R,7S,8aR)-6-Hydroxymethyl-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 palladium dihydroxide camphor-10-sulfonic acid 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4aR,6S,7R,8aS)-6-Hydroxymethyl-2,2,4a-trimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
  参考文献：
  名称：

  Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.

  DOI：

  10.1021/ol026804w

文献信息

• Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin
  作者：Keisuke Suzuki、Tadashi Nakata

  DOI：10.1021/ol026804w

  日期：2002.10.1

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.