N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide | 213192-07-5

• 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-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide
• CAS: 213192-07-5
• 化学式: C₄₆H₅₆N₄O₁₂
• 分子量: 856.97
• InChiKey: KSAIMOXBSRFBKN-YGCZQQNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  62.0
• 可旋转键数：
  24.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  201.39
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  perbenzyl fucosyl bromide 、 N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide 在 四乙基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以58%的产率得到5-azido-3-oxapentyl 2-acetamino-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl]-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  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-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 在 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.33h， 生成 N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-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