(3S,4R)-3-methyl-1-[(1R,2S,5S)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]oct-6-yn-4-ol | 585526-37-0

• 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: (3S,4R)-3-methyl-1-[(1R,2S,5S)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]oct-6-yn-4-ol
• CAS: 585526-37-0
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: WKJMAGKBMGTXAP-QMHWVQJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-methyl-1-[(1R,2S,5S)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]oct-6-yn-4-ol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,6R,8R,9S)-8-but-2-ynyl-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]methanol 、 [(2R,3S,6S,8R,9S)-8-but-2-ynyl-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]methanol
  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 、 正丁基锂 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 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 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4R)-3-methyl-1-[(1R,2S,5S)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]oct-6-yn-4-ol
  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

文献信息

• Efficient synthesis of the 6,6-spiroacetal of spirofungin A
  作者：Takeshi Shimizu、Junichi Kusaka、Haruaki Ishiyama、Tadashi Nakata

  DOI：10.1016/s0040-4039(03)01184-5

  日期：2003.6

  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.