N-[(2R,3R,4R,5S,6R)-2-[2-(2-Amino-ethoxy)-ethoxy]-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide | 213192-11-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R,4R,5S,6R)-2-[2-(2-Amino-ethoxy)-ethoxy]-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS: 213192-11-1
• 化学式: C₂₄H₄₄N₂O₁₆
• 分子量: 616.617
• InChiKey: KKOWBPFGUUXICW-UFTSTOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  281.57
• 氢给体数：
  10.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  3-马来酰亚胺基丙酸羟基琥珀酰亚胺酯 、 N-[(2R,3R,4R,5S,6R)-2-[2-(2-Amino-ethoxy)-ethoxy]-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal 四乙基溴化铵 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 64.0h， 生成 N-[(2R,3R,4R,5S,6R)-2-[2-(2-Amino-ethoxy)-ethoxy]-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Synthesis of Le^X and Le^Y Oligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups

  摘要：

  5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc and the tetrasaccharide alpha-L-Fuc-alpha-(1-->2)-beta-D-Gal-(1-->4)-[alpha-L-Fuc-(1-->3)]-GlcNAc that represent the epitopes defining the human blood groups Le(x) and Le(y). The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

  DOI：

  10.1080/07328309808007459