(R)-7-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-heptanoic acid methyl ester | 201472-32-4

• 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: (R)-7-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-heptanoic acid methyl ester
• 英文别名: methyl (6R)-7-[tert-butyl(diphenyl)silyl]oxy-6-hydroxyheptanoate
• CAS: 201472-32-4
• 化学式: C₂₄H₃₄O₄Si
• 分子量: 414.617
• InChiKey: BYKYZKSTAXDCPF-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-7-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-heptanoic acid methyl ester 在 disodium hydrogenphosphate 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium amalgam 、 三丁基膦 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.75h， 生成 (2R,13R)-2,8-bis(methoxymethoxy)-13-[(2S,5S)-5-[(1S)-1-(methoxymethoxy)tridecyl]oxolan-2-yl]-13-(phenylmethoxymethoxy)tridecan-1-ol
  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：

  (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 苯甲酸 作用下， 以 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 17.0h， 生成 (R)-7-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-heptanoic acid methyl ester
  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.