methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate | 351530-33-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate
• CAS: 351530-33-1
• 化学式: C₅₃H₆₃Cl₃N₂O₁₇
• 分子量: 1106.45
• InChiKey: NONDDRGCMPXWHM-CSWJWASISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  75.0
• 可旋转键数：
  23.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  239.83
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-hydroxyoctyl)-β-D-galactopyranosyl]-(1->4)-[4-methoxyphenyl 2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranosid]uronate 、 methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到
  参考文献：
  名称：

  Synthesis of linear-type chondroitin clusters having a C8 spacer between disaccharide moieties and enzymatic transfer of d-glucuronic acid to the artificial glycans

  摘要：

  Newly designed linear-type glycoclusters were synthesized which involve a chondroitin repeating disaccharide ligand and a hydrophobic octyl ether spacer. The spacer mimics the corresponding disaccharide unit. Repeating elongation of the pseudo-tetrasaccharide that was derived from the common cluster unit [--> 8)-octyl-(1 --> 3)-beta -D-Gal-NAc-(1 --> 4)-beta -D-GlcA-(1 -->] allowed the syntheses of up to the pseudo-decasaccharide analog of chondroitin. An enzymatic D-GlcA transfer at the non-reducing end of the synthesized artificial glycans by GlcATase II was observed. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00071-4
• 作为产物：
  描述：

  4-methoxyphenyl O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-6-O-tert-butyldiphenylsilyl-2,3-di-O-(4-methylbenzoyl)-β-D-glucopyranoside 在 Lindlar's catalyst 吡啶 、 sodium chlorite 、 2-甲基-2-丁烯 、 草酰氯 、 ammonium cerium(IV) nitrate 、 四丁基氟化铵 、 氢气 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 101.58h， 生成 methyl [2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(8-levulinoyloxyoctyl)-β-D-galactopyranosyl]-(1->4)-[2,3-di-O-(4-methylbenzoyl)-α-D-glucopyranosyl trichloroacetamidate]uronate
  参考文献：
  名称：

  Synthesis of linear-type chondroitin clusters having a C8 spacer between disaccharide moieties and enzymatic transfer of d-glucuronic acid to the artificial glycans

  摘要：

  Newly designed linear-type glycoclusters were synthesized which involve a chondroitin repeating disaccharide ligand and a hydrophobic octyl ether spacer. The spacer mimics the corresponding disaccharide unit. Repeating elongation of the pseudo-tetrasaccharide that was derived from the common cluster unit [--> 8)-octyl-(1 --> 3)-beta -D-Gal-NAc-(1 --> 4)-beta -D-GlcA-(1 -->] allowed the syntheses of up to the pseudo-decasaccharide analog of chondroitin. An enzymatic D-GlcA transfer at the non-reducing end of the synthesized artificial glycans by GlcATase II was observed. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00071-4