1',2,3',4',6'-pentakis-O-(3-methylbutanoyl)-β-D-fructofuranosyl α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1',2,3',4',6'-pentakis-O-(3-methylbutanoyl)-β-D-fructofuranosyl α-D-glucopyranoside
• 英文别名: atractysucrose-I；[(2R,3R,4S,5S)-5-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)oxan-2-yl]oxy-3,4-bis(3-methylbutanoyloxy)-5-(3-methylbutanoyloxymethyl)oxolan-2-yl]methyl 3-methylbutanoate
• 化学式: C₃₇H₆₂O₁₆
• 分子量: 762.89
• InChiKey: SDEMGAHEVRWAGR-PLLRUHFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  53
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  220
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1',2,3',4',6'-pentakis-O-(3-methylbutanoyl)-β-D-fructofuranosyl α-D-glucopyranoside 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3R,4S,5S)-5-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(3-methylbutanoyloxy)oxan-2-yl]oxy-3,4-bis(3-methylbutanoyloxy)-5-(3-methylbutanoyloxymethyl)oxolan-2-yl]methyl 3-methylbutanoate
  参考文献：
  名称：

  Facilely accessible multidrug resistance modulator derived from sucrose

  摘要：

  Exploration for new MDR-modulators utilizing atractysucroses as scaffolds disclosed 2,3,4,3,4'-O--pentaisovalerylsucrose (9) as a readily accessible medicinal lead. This lead was prepared from sucrose in 65% total yield for three steps. In addition, compound 9 exhibited more potent MDR modulating activity than verapamil, a representative modulator of MDR mediated by P-gp. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00702-3

文献信息

• Stigmastane derivatives and isovaleryl sucrose esters from Vernonia guineensis (Asteraceae)
  作者：Alembert T Tchinda、Pierre Tane、Johnson F Ayafor、Joseph D Connolly

  DOI：10.1016/s0031-9422(03)00326-1

  日期：2003.8

  Vernoguinoside, 16beta,22R;21,23S-diepoxy-3beta-O-beta-D-glucopyranosyloxy-21S,24-dihydroxy-5alpha-stigmasta-8,14-dien-28-one (1), a new stigmastane derivative, 16beta,22R;21,23S-diepoxy-21S,24-dihydroxy-5alpha-stigmasta-8,14-diene-3,28-dione (2) and two new sucrose esters, 1',3,3',4',6'-pentakis-O-(3-methylbutanoyl)-beta-D-fructofuranosyl alpha-D-glucopyranoside (3) and 1,2,3',6,6'-pentakis-O-(3-methylbutanoyl)-beta-D-fructofuranosyl alpha-D-glucopyranoside (4), have been isolated from the stem bark of Vernonia guineensis. The structures of the new compounds were determined on the basis of spectroscopic evidence. (C) 2003 Elsevier Ltd. All rights reserved.
• Facilely accessible multidrug resistance modulator derived from sucrose
  作者：Nobutoshi Murakami、Satoru Tamura、Etsuko Iwata、Shunji Aoki、Shin-ichi Akiyama、Motomasa Kobayashi

  DOI：10.1016/s0960-894x(02)00702-3

  日期：2002.11

  Exploration for new MDR-modulators utilizing atractysucroses as scaffolds disclosed 2,3,4,3,4'-O--pentaisovalerylsucrose (9) as a readily accessible medicinal lead. This lead was prepared from sucrose in 65% total yield for three steps. In addition, compound 9 exhibited more potent MDR modulating activity than verapamil, a representative modulator of MDR mediated by P-gp. (C) 2002 Elsevier Science Ltd. All rights reserved.