(2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyl-2-(prop-2-ynyl)tetrahydropyran | 632354-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyl-2-(prop-2-ynyl)tetrahydropyran
• 英文别名: tert-butyl-dimethyl-[(2S,3R,5S,6R)-6-methyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)-2-prop-2-ynyloxan-3-yl]oxysilane
• CAS: 632354-38-2
• 化学式: C₃₁H₄₄O₄Si
• 分子量: 508.773
• InChiKey: XFJXYPDYPMXYPH-ZNHAZFDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyl-2-(prop-2-ynyl)tetrahydropyran 在 ruthenium(IV) oxide 、 sodium periodate 、 正丁基锂 作用下， 以 四氢呋喃 、 四氯化碳 、 六甲基磷酰三胺 、 正己烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 1-[(2S,3R,5S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methyl-5-phenylmethoxy-6-(2-phenylmethoxyethyl)oxan-2-yl]-4-[(1S,3R,5S,6R,8S,11R,13S,18R)-5-[tert-butyl(dimethyl)silyl]oxy-11,13,16,16-tetramethyl-2,7,12,15,17-pentaoxatetracyclo[9.8.0.03,8.013,18]nonadecan-6-yl]butane-2,3-dione
  参考文献：
  名称：

  Sulfonyl-Stabilized Oxiranyllithium-Based Approach to Polycyclic Ethers. Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.

  DOI：

  10.1021/jo035145d
• 作为产物：
  描述：

  (4R,5S)-4-[(2S,3R)-3-(2-benzyloxyethyl)-3-methyl-2-(toluene-4-sulfonyl)oxiranylmethyl]-2,2-di-tert-butyl-5-(triethylsilyloxy)-[1,3,2]dioxasilinane 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 63.5h， 生成 (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyl-2-(prop-2-ynyl)tetrahydropyran
  参考文献：
  名称：

  Sulfonyl-Stabilized Oxiranyllithium-Based Approach to Polycyclic Ethers. Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.

  DOI：

  10.1021/jo035145d