allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside | 418764-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: Fuc2Me3Ac4Ac(a1-2)Gal3Ac4Ac6Ac(b)-O-allyl；[(2R,3S,4S,5R,6R)-3,4-diacetyloxy-5-[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-3-methoxy-6-methyloxan-2-yl]oxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 418764-40-6
• 化学式: C₂₆H₃₈O₁₅
• 分子量: 590.579
• InChiKey: JPULSPBKVBQVLZ-FVLMCRTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到allyl 2-O-methyl-α-L-fucopyranosyl-(1->2)-β-D-galactopyranoside
  参考文献：
  名称：

  SYNTHESIS OF O-METHYLATED DISACCHARIDES RELATED TO EXCRETORY/ SECRETORY ANTIGENS OF TOXOCARA LARVAE1

  摘要：

  The disaccharides 2-O-Me-alpha -L-Fucp-(1 -->2)-beta -D-Galp-(1 --> OAllyl) 12, alpha -L-Fucp-(1 -->2)-4-O-Me-beta -D-Galp-(1 --> OAllyl) 15, and 2-O-Me-alpha -L-Fucp-(1 -->2)-4-O-Me-beta -D-Galp-(1 --> OAllyl) 18 have been synthesized. Glycosylation reactions were performed using ethyl 1-thiofueopyranosides as glycosyl donors and N-iodosuceiniinide-triflic acid as the activating agent. The O-methylated disaccharides correspond to highly immunogenic O-glycan antigens occurring at the surface of Toxocara canis and Toxocara cati larvae.

  DOI：

  10.1081/car-100108285
• 作为产物：
  描述：

  allyl 4,6-O-p-methoxybenzylidene-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 二正丁基氧化锡 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  SYNTHESIS OF O-METHYLATED DISACCHARIDES RELATED TO EXCRETORY/ SECRETORY ANTIGENS OF TOXOCARA LARVAE1

  摘要：

  The disaccharides 2-O-Me-alpha -L-Fucp-(1 -->2)-beta -D-Galp-(1 --> OAllyl) 12, alpha -L-Fucp-(1 -->2)-4-O-Me-beta -D-Galp-(1 --> OAllyl) 15, and 2-O-Me-alpha -L-Fucp-(1 -->2)-4-O-Me-beta -D-Galp-(1 --> OAllyl) 18 have been synthesized. Glycosylation reactions were performed using ethyl 1-thiofueopyranosides as glycosyl donors and N-iodosuceiniinide-triflic acid as the activating agent. The O-methylated disaccharides correspond to highly immunogenic O-glycan antigens occurring at the surface of Toxocara canis and Toxocara cati larvae.

  DOI：

  10.1081/car-100108285