phenyl [methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate]-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl (2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranoside)uronate | 904313-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl [methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate]-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl (2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranoside)uronate
• CAS: 904313-31-1
• 化学式: C₆₈H₆₉N₃O₂₁S
• 分子量: 1296.37
• InChiKey: MHTNMOFNGMCWON-DJLSLBNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  93.0
• 可旋转键数：
  28.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  297.47
• 氢给体数：
  0.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  phenyl [methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate]-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl (2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranoside)uronate 、 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到methyl (2R,3S,4S,5R,6R)-3-[(2R,3R,4R,5S,6R)-6-(acetyloxymethyl)-3-azido-5-[(2R,3R,4S,5S,6R)-3-benzoyloxy-6-methoxycarbonyl-5-(4-oxopentanoyloxy)-4-phenylmethoxyoxan-2-yl]oxy-4-phenylmethoxyoxan-2-yl]oxy-6-[(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-5-azido-6-methoxy-4-phenylmethoxyoxan-3-yl]oxy-5-benzoyloxy-4-phenylmethoxyoxane-2-carboxylate
  参考文献：
  名称：

  Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors

  摘要：

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.020
• 作为产物：
  描述：

  methyl (2R,3S,4S,5R,6S)-5-benzoyloxy-3-(4-oxopentanoyloxy)-4-phenylmethoxy-6-phenylsulfanyloxane-2-carboxylate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 phenyl [methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate]-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl (2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranoside)uronate
  参考文献：
  名称：

  Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors

  摘要：

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.020