(1'''R,2'R,2''R,5'R,5''R)-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]methanol | 286853-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'''R,2'R,2''R,5'R,5''R)-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]methanol
• 英文别名: [(2R,5R)-5-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-15-phenylmethoxypentadecyl]oxolan-2-yl]oxolan-2-yl]methanol
• CAS: 286853-92-7
• 化学式: C₃₇H₆₆O₅Si
• 分子量: 619.014
• InChiKey: QXLVNZSKQAWDGM-JZPVOVDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.75
• 重原子数：
  43
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'''R,2'R,2''R,5'R,5''R)-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]methanol 在 palladium on activated charcoal sodium chlorite 、 lutidine 、 camphor-10-sulfonic acid 、 氢氟酸 、 氢气 、 双(三甲基硅烷基)氨基钾 、 magnesium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 乙酸乙酯 、 异丙醇 、 乙腈 、 叔丁醇 为溶剂， 生成 (5S)-3-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-二羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]-13-羟基十三烷基]-5-甲基-5H-呋喃-2-酮
  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：

  (1R,2'R,2''R,5'R,5''R)-1-[5'-(5''-(tert-butyldimethylsilyloxy)methyltetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]-1-(tert-butyldimethylsilyloxy)-15-benzyloxypentadecan-1-one 在 甲醇 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57%的产率得到(1'''R,2'R,2''R,5'R,5''R)-[5'-(5''-(1'''-tert-butyldimethylsilyloxy-15'''-benzyloxypentadec-1'''-yl)tetrahydrofuran-2''-yl)tetrahydrofuran-2'-yl]methanol
  参考文献：
  名称：

  Total Syntheses of Squamocin A and Squamocin D, Bi-tetrahydrofuran Acetogenins from Annonaceae

  摘要：

  DOI：

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

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