(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2R,3S,4R,5R)-2-acetoxymethyl-5-azido-4-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester | 247077-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2R,3S,4R,5R)-2-acetoxymethyl-5-azido-4-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 247077-99-2
• 化学式: C₃₀H₃₅Cl₃N₄O₁₅
• 分子量: 797.985
• InChiKey: JKBVFGQYKGCGOB-GZRQAONGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  250.26
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl [methyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate 、 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2R,3S,4R,5R)-2-acetoxymethyl-5-azido-4-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4 A molecular sieve 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以64%的产率得到
  参考文献：
  名称：

  A synthetic heparan sulfate pentasaccharide, exclusively containing l -iduronic acid, displays higher affinity for FGF-2 than its d -glucuronic acid-containing isomers

  摘要：

  It has been suggested that the FGF-2 binding site on heparan sulfate chains is a trisulfated pentasaccharide containing three hexuronic acid units. The configuration at C-5 of two of them being undetermined, we have synthesized the four possible pentasaccharides, and have evaluated their FGF-2 binding affinity through in vitro biological assays. The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00106-6
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 potassium carbonate 、 苄胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2R,3S,4R,5R)-2-acetoxymethyl-5-azido-4-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A synthetic heparan sulfate pentasaccharide, exclusively containing l -iduronic acid, displays higher affinity for FGF-2 than its d -glucuronic acid-containing isomers

  摘要：

  It has been suggested that the FGF-2 binding site on heparan sulfate chains is a trisulfated pentasaccharide containing three hexuronic acid units. The configuration at C-5 of two of them being undetermined, we have synthesized the four possible pentasaccharides, and have evaluated their FGF-2 binding affinity through in vitro biological assays. The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00106-6