methyl (6R)-6-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-6-(phenylmethoxymethoxy)hexanoate | 201472-15-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (6R)-6-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-6-(phenylmethoxymethoxy)hexanoate
• CAS: 201472-15-3
• 化学式: C₃₂H₅₄O₆
• 分子量: 534.777
• InChiKey: PCXMPBPSJQJPHH-MBEDZMRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  38
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (6R)-6-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-6-(phenylmethoxymethoxy)hexanoate 在 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丙基高钌酸铵 、 sodium amalgam 、 三甲基溴硅烷 、 4 A molecular sieve 、 TEA 、 camphor-10-sulfonic acid 、 甲基磺酰氯 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 45.25h， 生成 (2S)-2-methyl-4-[(2R,13R)-2,8,13-trihydroxy-13-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
  参考文献：
  名称：

  Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin:  Pseudoannonacin A?

  摘要：

  A stereocontrolled first total synthesis of a diastereomer of the presumed mono-tetrahydrofuran type acetogenin annonacin A, starting with enantiomerically pure precursors, is described. The absolute stereochemistry of the C-15-C-20 segment corresponding to the tetrahydrofuran ring of the natural product was secured by X-ray crystal structure analysis of an advanced intermediate. The synthetic product (a mixture of epimers at C-10) had spectroscopic data identical to that of the natural product, but a different optical rotation.

  DOI：

  10.1021/jo9713621
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 TEA 、 三氟化硼乙醚 、 氢气 、 乙酸酐 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三苯基膦 、 苯甲酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 80.75h， 生成 methyl (6R)-6-[(2S,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-6-(phenylmethoxymethoxy)hexanoate
  参考文献：
  名称：

  Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin:  Pseudoannonacin A?

  摘要：

  A stereocontrolled first total synthesis of a diastereomer of the presumed mono-tetrahydrofuran type acetogenin annonacin A, starting with enantiomerically pure precursors, is described. The absolute stereochemistry of the C-15-C-20 segment corresponding to the tetrahydrofuran ring of the natural product was secured by X-ray crystal structure analysis of an advanced intermediate. The synthetic product (a mixture of epimers at C-10) had spectroscopic data identical to that of the natural product, but a different optical rotation.

  DOI：

  10.1021/jo9713621

文献信息

• Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin:  Pseudoannonacin A?
  作者：Stephen Hanessian、Teresa Abad Grillo

  DOI：10.1021/jo9713621

  日期：1998.2.1

  A stereocontrolled first total synthesis of a diastereomer of the presumed mono-tetrahydrofuran type acetogenin annonacin A, starting with enantiomerically pure precursors, is described. The absolute stereochemistry of the C-15-C-20 segment corresponding to the tetrahydrofuran ring of the natural product was secured by X-ray crystal structure analysis of an advanced intermediate. The synthetic product (a mixture of epimers at C-10) had spectroscopic data identical to that of the natural product, but a different optical rotation.