octyl (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)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside | 1379585-72-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl (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)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: prop-2-enyl (2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-2-(acetyloxymethyl)-6-[(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-5-azido-6-octoxy-4-phenylmethoxyoxan-3-yl]oxy-2-methoxycarbonyl-4,5-bis(phenylmethoxy)oxan-3-yl]oxy-5-azido-4-phenylmethoxyoxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 1379585-72-4
• 化学式: C₈₉H₁₀₄N₆O₂₃
• 分子量: 1625.83
• InChiKey: SVWAPEGTWVVVAX-RMHWAMCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  118
• 可旋转键数：
  49
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  272
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  octyl (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)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 在 lithium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以23.1 mg的产率得到
  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
• 作为产物：
  描述：

  辛醇 、 (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)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以67%的产率得到octyl (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)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
  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