(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose | 1379585-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
• 英文别名: prop-2-enyl (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-5-azido-6-[(2S,3S,4S,5R,6R)-6-[[(1R,2S,3R,4R,5R)-4-azido-3-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-2-methoxycarbonyl-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-4-phenylmethoxyoxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 1379585-68-8
• 化学式: C₇₉H₈₄N₆O₂₁
• 分子量: 1453.56
• InChiKey: LCHMBCOXHFBWPI-RTLNMDMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  106
• 可旋转键数：
  38
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  246
• 氢给体数：
  0
• 氢受体数：
  25

反应信息

• 作为产物：
  描述：

  (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 、 (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 7.5h， 以43%的产率得到(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of heparan sulfate tetrasaccharide as a substrate for human heparanase

  摘要：

  Regiospecifically sulfated heparan sulfate tetrasaccharide, GlcA beta-GlcN(NS6S)alpha-GlcA beta-GlcN(NS6S)alpha was first synthesized as an octyl glycoside. Total synthesis was achieved effectively by coupling the corresponding disaccharide units in short steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.014