ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside | 760190-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside
• CAS: 760190-17-8
• 化学式: C₂₃H₃₈O₅SSi
• 分子量: 454.703
• InChiKey: XXBWVJNHZHLAST-LOONRQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 氟化氢吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.83h， 生成 octyl 4-O-acetyl-2-O-benzyl-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and biological activities of octyl 2,3-di-O-sulfo-α-l-fucopyranosyl-(1→3)-2-O-sulfo-α-l-fucopyranosyl-(1→4)-2,3-di-O-sulfo-α-l-fucopyranosyl-(1→3)-2-O-sulfo-α-l-fucopyranosyl-(1→4)-2,3-di-O-sulfo-β-l-fucopyranoside

  摘要：

  Octyl 2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1 --> 3)-2-O-sulfo-alpha-L-fucopyranosyl-(1 --> 4)-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1 --> 3)-2-O-sulfo-alpha-L-fucopyranosyl-(1 --> 4)-2,3-di-O-sulfo-beta-L-fucopyranoside, a fucosyl pentasaccharide with a regular structure resembling the repeating unit of a natural sulfated fucan, was chemically synthesized using a convergent '2 + 3' strategy. Regioselective 3-O-silylation of beta-thiofucopyranoside and AgOTf-catalyzed glycosylation of the protected glycosyl trichloroacetimidate facilitated a one-pot trisaccharide synthesis. The synthesized target compound showed good antitumor activity in vivo, and promising anticoagulant activity in vitro. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.006
• 作为产物：
  描述：

  ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and biological activities of octyl 2,3-di-O-sulfo-α-l-fucopyranosyl-(1→3)-2-O-sulfo-α-l-fucopyranosyl-(1→4)-2,3-di-O-sulfo-α-l-fucopyranosyl-(1→3)-2-O-sulfo-α-l-fucopyranosyl-(1→4)-2,3-di-O-sulfo-β-l-fucopyranoside

  摘要：

  Octyl 2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1 --> 3)-2-O-sulfo-alpha-L-fucopyranosyl-(1 --> 4)-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1 --> 3)-2-O-sulfo-alpha-L-fucopyranosyl-(1 --> 4)-2,3-di-O-sulfo-beta-L-fucopyranoside, a fucosyl pentasaccharide with a regular structure resembling the repeating unit of a natural sulfated fucan, was chemically synthesized using a convergent '2 + 3' strategy. Regioselective 3-O-silylation of beta-thiofucopyranoside and AgOTf-catalyzed glycosylation of the protected glycosyl trichloroacetimidate facilitated a one-pot trisaccharide synthesis. The synthesized target compound showed good antitumor activity in vivo, and promising anticoagulant activity in vitro. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.006