methyl {(2S,3R,5R)-5-[(1S,2S)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate | 537007-37-7

• 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: methyl {(2S,3R,5R)-5-[(1S,2S)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate
• CAS: 537007-37-7
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: CSNZYLPSIOHYSW-UXMQXVNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 methyl {(2S,3R,5R)-5-[(1S,2S)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-1-((2R,4R,5S)-5-methoxycarbonylmethyl-4-methyl-tetrahydro-furan-2-yl)-3-methyl-2-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-3-enyl ester
  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：

  methyl {(2S,3R,5R)-5-[(1R,2S)-1,2-isopropylidenedioxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以80%的产率得到methyl {(2S,3R,5R)-5-[(1S,2S)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate
  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