4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate | 760190-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate
• CAS: 760190-20-3
• 化学式: C₂₃H₃₄Cl₃NO₆Si
• 分子量: 554.971
• InChiKey: SYFDYZUZPJBHLB-JLTFKRJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  87.07
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 silver trifluoromethanesulfonate 、 氟化氢吡啶 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 octyl 4-O-acetyl-2-O-benzyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-benzyl-α-L-fucopyranosyl-(1->3)-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：

  (2S,3R,4R,5S,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-3-ol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 7.17h， 生成 4-O-acetyl-2-O-benzyl-3-O-tert-butyldimethylsilyl-β-L-fucopyranosyl trichloroacetimidate
  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