(1R)-1-{(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-2-propen-1-ol | 537007-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1R)-1-{(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-2-propen-1-ol
• 英文别名: (1R)-1-[(2R,4R,5S)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-4-methyloxolan-2-yl]prop-2-en-1-ol
• CAS: 537007-23-1
• 化学式: C₁₆H₃₂O₃Si
• 分子量: 300.514
• InChiKey: IAYUUYVLLIBIRA-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• 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：

  (1R)-1-{(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-2-propen-1-ol 在 咪唑 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 potassium phosphate buffer 、 pyridine-SO3 complex 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 28.5h， 生成 [(2S,3R,5R)-5-((4S,5R)-5-Isopropenyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-tetrahydro-furan-2-yl]-acetaldehyde
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x
• 作为产物：
  描述：

  {(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-methanol 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1R)-1-{(2R,4R,5S)-5-[2-(tert-butyldimethylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-2-propen-1-ol
  参考文献：
  名称：

  Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments

  摘要：

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00142-x

文献信息

• Absolute stereochemistry of amphidinolide C: synthesis of C-1–C-10 and C-17–C-29 segments
  作者：Takaaki Kubota、Masashi Tsuda、Jun'ichi Kobayashi

  DOI：10.1016/s0040-4020(03)00142-x

  日期：2003.3

  Two of each diastereomers of the C-1-C-10 and C-17-C-29 segments of amphidinolide C (1) were synthesized. Comparing the H-1 NMR chemical shifts of its MTPA esters with those of linear methyl ester of 1, the absolute configurations at C-7, C-8, C-20, C-23, and C-24 in amphidinolide C (1) were confirmed to be all R. (C) 2003 Elsevier Science Ltd. All rights reserved.