methyl {3-[2-(2,3,4-tri-O-acetyl-β-L-fucopyranosyloxy)ethoxy]propyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranoside}onate | 188176-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl {3-[2-(2,3,4-tri-O-acetyl-β-L-fucopyranosyloxy)ethoxy]propyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranoside}onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[3-[2-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyethoxy]propoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 188176-75-2
• 化学式: C₃₇H₅₅NO₂₂
• 分子量: 865.837
• InChiKey: AUPRDYCDQKHAAJ-DNWYYBAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  60.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  285.65
• 氢给体数：
  1.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  methyl {3-[2-(2,3,4-tri-O-acetyl-β-L-fucopyranosyloxy)ethoxy]propyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranoside}onate 在 sodium methylate 、 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以78%的产率得到3-[2-(β-L-fucopyranosyloxy)ethoxy]propyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid
  参考文献：
  名称：

  Synthesis of Sialyl Lewis x Analogues 2

  摘要：

  Sialyl Lewis X (SLe(X) analogues) containing beta-1-fucopyranosyl residues with an alkyl [-(CH2)(6)-] (1a), a heteroalkyl [-(CH2)(2)-O-(CH2)(3)-] (Ib)or a heterocycloalkyl [-2-cyclohexyl-O-(CH,),-] (2a) moiety were synthesised by silver ion promoted glycosylation. Further analogues where sialic acid was replaced by a second beta-L-fucopyranosyl (3a, 3b) or hydrogensulphate unit (4a, 4b) were also prepared.

  DOI：

  10.1080/07328309708006507
• 作为产物：
  描述：

  2-(3-benzyloxypropoxy)ethanol 在 palladium on activated charcoal 氢气 、 silver salicylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 34.0h， 生成 methyl {3-[2-(2,3,4-tri-O-acetyl-β-L-fucopyranosyloxy)ethoxy]propyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranoside}onate
  参考文献：
  名称：

  Synthesis of Sialyl Lewis x Analogues 2

  摘要：

  Sialyl Lewis X (SLe(X) analogues) containing beta-1-fucopyranosyl residues with an alkyl [-(CH2)(6)-] (1a), a heteroalkyl [-(CH2)(2)-O-(CH2)(3)-] (Ib)or a heterocycloalkyl [-2-cyclohexyl-O-(CH,),-] (2a) moiety were synthesised by silver ion promoted glycosylation. Further analogues where sialic acid was replaced by a second beta-L-fucopyranosyl (3a, 3b) or hydrogensulphate unit (4a, 4b) were also prepared.

  DOI：

  10.1080/07328309708006507