methyl {(2S,3R,5R)-5-[(1R,2R)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate | 537007-12-8

• 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-[(1R,2R)-1,2-dihydroxy-3-methyl-3-butenyl]-3-methyltetrahydrofuran-2-yl}-acetate
• 英文别名: methyl 2-[(2S,3R,5R)-5-[(1R,2R)-1,2-dihydroxy-3-methylbut-3-enyl]-3-methyloxolan-2-yl]acetate
• CAS: 537007-12-8
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: CSNZYLPSIOHYSW-TUFGJSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 methyl {(2S,3R,5R)-5-[(1R,2R)-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81%的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-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：

  (2R,4R,5S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-tetrahydro-furan-2-carbaldehyde 在 咪唑 、 sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 、 四氧化锇 、 N-甲基吲哚酮 、 2-甲基-2-丁烯 、 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 、 甲醇 、 乙醚 、 正己烷 、 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 36.5h， 生成 methyl {(2S,3R,5R)-5-[(1R,2R)-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

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.