(5S,13'R,2''R,5''R,2'''R,5'''R,1''''R,5''''S)-3-[13'-(5''-(5'''-(1'''',5''''-bis(tert-butyldimethylsilyloxy)undec-1''''-yl)tetrahydrofuran-2'''-yl)tetrahydrofuran-2''-yl)-13'-(tert-butyldimethylsilyloxy)tridec-1-yl]-5-methylfuran-2(5H)-one | 286853-96-1

• 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: (5S,13'R,2''R,5''R,2'''R,5'''R,1''''R,5''''S)-3-[13'-(5''-(5'''-(1'''',5''''-bis(tert-butyldimethylsilyloxy)undec-1''''-yl)tetrahydrofuran-2'''-yl)tetrahydrofuran-2''-yl)-13'-(tert-butyldimethylsilyloxy)tridec-1-yl]-5-methylfuran-2(5H)-one
• 英文别名: (2S)-4-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1R,5S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]undecyl]oxolan-2-yl]oxolan-2-yl]-13-[tert-butyl(dimethyl)silyl]oxytridecyl]-2-methyl-2H-furan-5-one
• CAS: 286853-96-1
• 化学式: C₅₅H₁₀₈O₇Si₃
• 分子量: 965.715
• InChiKey: YAWRDYFDRFEFLA-YORCOMSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.95
• 重原子数：
  65
• 可旋转键数：
  34
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,13'R,2''R,5''R,2'''R,5'''R,1''''R,5''''S)-3-[13'-(5''-(5'''-(1'''',5''''-bis(tert-butyldimethylsilyloxy)undec-1''''-yl)tetrahydrofuran-2'''-yl)tetrahydrofuran-2''-yl)-13'-(tert-butyldimethylsilyloxy)tridec-1-yl]-5-methylfuran-2(5H)-one 在 氢氟酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 Squamocin D
  参考文献：
  名称：

  Total syntheses of squamocin A and squamocin D

  摘要：

  The total syntheses of two acetogenins, squamocin A and squamocin D, have been achieved. The adjacent bis-THF subunit was constructed by a multiple Williamson reaction. The left and the right side chain were added by addition of organomagnesium compounds to aldehyde functions. The conversion of a carboxylic acid into the butenolide moiety concluded both syntheses. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01225-3
• 作为产物：
  描述：

  (S)-(+)-1-Decen-3-ol 在 palladium on activated charcoal 吡啶 、 咪唑 、 sodium chlorite 、 9-borabicyclo[3.3.1]nonane dimer 、 lutidine 、 camphor-10-sulfonic acid 、 氢气 、 双(三甲基硅烷基)氨基钾 、 magnesium 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 乙酸乙酯 、 异丙醇 、 叔丁醇 为溶剂， 生成 (5S,13'R,2''R,5''R,2'''R,5'''R,1''''R,5''''S)-3-[13'-(5''-(5'''-(1'''',5''''-bis(tert-butyldimethylsilyloxy)undec-1''''-yl)tetrahydrofuran-2'''-yl)tetrahydrofuran-2''-yl)-13'-(tert-butyldimethylsilyloxy)tridec-1-yl]-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Total syntheses of squamocin A and squamocin D

  摘要：

  The total syntheses of two acetogenins, squamocin A and squamocin D, have been achieved. The adjacent bis-THF subunit was constructed by a multiple Williamson reaction. The left and the right side chain were added by addition of organomagnesium compounds to aldehyde functions. The conversion of a carboxylic acid into the butenolide moiety concluded both syntheses. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01225-3

文献信息

• Total syntheses of squamocin A and squamocin D
  作者：Ulrich Emde、Ulrich Koert

  DOI：10.1016/s0040-4039(99)01225-3

  日期：1999.8

  The total syntheses of two acetogenins, squamocin A and squamocin D, have been achieved. The adjacent bis-THF subunit was constructed by a multiple Williamson reaction. The left and the right side chain were added by addition of organomagnesium compounds to aldehyde functions. The conversion of a carboxylic acid into the butenolide moiety concluded both syntheses. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Total Syntheses of Squamocin A and Squamocin D, Bi-tetrahydrofuran Acetogenins from Annonaceae
  作者：Ulrich Emde、Ulrich Koert

  DOI：10.1002/(sici)1099-0690(200005)2000:10<1889::aid-ejoc1889>3.0.co;2-r

  日期：2000.5