[(2R,3S)-1-hydroxy-3-methyl-5-[(1R,2S,5R)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentan-2-yl] methanesulfonate | 585526-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: [(2R,3S)-1-hydroxy-3-methyl-5-[(1R,2S,5R)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentan-2-yl] methanesulfonate
• CAS: 585526-35-8
• 化学式: C₁₄H₂₆O₆S
• 分子量: 322.423
• InChiKey: ZZPIKECVNKWGBE-PEDHHIEDSA-N

物化性质

• 沸点：
  472.3±25.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-1-hydroxy-3-methyl-5-[(1R,2S,5R)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentan-2-yl] methanesulfonate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以93%的产率得到(1R,2S,5R)-2-methyl-5-[(3S)-3-[(2S)-oxiran-2-yl]butyl]-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Efficient synthesis of the 6,6-spiroacetal of spirofungin A

  摘要：

  The 6,6-spiroacetal segment of spirofungin A, an antifungal antibiotic isolated from Streptomyces violaceusniger Tu 4113, was efficiently prepared via the coupling reaction of the Weinreb amide and the alkyne which are readily available from the common intermediate. The synthesis includes the unsymmetrization through a stereoinversion at the C11 position and the transacetalization as the key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01184-5
• 作为产物：
  描述：

  3R-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2R-methyl-butyraldehyde 在 palladium on activated charcoal 吡啶 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S)-1-hydroxy-3-methyl-5-[(1R,2S,5R)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]pentan-2-yl] methanesulfonate
  参考文献：
  名称：

  Efficient synthesis of the 6,6-spiroacetal of spirofungin A

  摘要：

  The 6,6-spiroacetal segment of spirofungin A, an antifungal antibiotic isolated from Streptomyces violaceusniger Tu 4113, was efficiently prepared via the coupling reaction of the Weinreb amide and the alkyne which are readily available from the common intermediate. The synthesis includes the unsymmetrization through a stereoinversion at the C11 position and the transacetalization as the key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01184-5