| 1187540-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1187540-84-6
• 化学式: C₁₆H₂₈O₅
• 分子量: 300.395
• InChiKey: JGLVDRGFWSCPCW-WVBBYLRTSA-N

反应信息

• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 16.25h， 生成 、
  参考文献：
  名称：

  Synthesis of the northern sector (C8–C19) of rapamycin via Chan rearrangement and oxidation of an α-acyloxyacetate

  摘要：

  Two routes to the masked tricarbonyl segment of the immunosuppressant rapamycin comprising C8-C19 were explored beginning from D-xylose. The first approach employed a protected form of 2,4,5-trihydroxypentanol to obtain dithiane 43, which failed to react with dimethyl oxalate to give a 1,2,3-tricarbonyl unit corresponding to the northern sector of rapamycin. A second approach employing carboxylic acid 61 derived from 43 utilized base-mediated (Chan) rearrangement of alpha-acyloxyacetate 62 with trapping of the resultant enediolate as bis silyl ether 63. Epoxidation of this diene afforded masked tri-keto ester 65 which underwent acid-catalyzed methanolysis to produce cyclic ketal 67. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.026