(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 | 1379585-71-3

• 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-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
• CAS: 1379585-71-3
• 化学式: C₈₃H₈₈Cl₃N₇O₂₃
• 分子量: 1658.0
• InChiKey: LQFDAIYUEKOXFV-CPSVFSOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.89
• 重原子数：
  116.0
• 可旋转键数：
  38.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  365.02
• 氢给体数：
  1.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (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-D-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%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)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
  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