ethyl 2,3-di-O-benzyl-4-O-chloroacetyl-1-thio-β-L-fucopyranoside | 760190-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-benzyl-4-O-chloroacetyl-1-thio-β-L-fucopyranoside
• CAS: 760190-15-6
• 化学式: C₂₄H₂₉ClO₅S
• 分子量: 465.01
• InChiKey: DLTOKAWXEORSFE-JYZZCPHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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 2,3-di-O-benzyl-4-O-chloroacetyl-1-thio-β-L-fucopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 生成 Chloro-acetic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-bromo-2-methyl-tetrahydro-pyran-3-yl ester
  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 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 33.0h， 生成 ethyl 2,3-di-O-benzyl-4-O-chloroacetyl-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