allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside | 418764-42-8

• 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)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside
• 英文别名: Mob(-2)Fuc3Ac4Ac(a1-2)[Mob(-3)][Mob(-6)]Gal4Me(b)-O-allyl；[(2S,3R,4R,5S,6S)-4-acetyloxy-6-[(2R,3R,4S,5S,6R)-5-methoxy-4-[(4-methoxyphenyl)methoxy]-6-[(4-methoxyphenyl)methoxymethyl]-2-prop-2-enoxyoxan-3-yl]oxy-5-[(4-methoxyphenyl)methoxy]-2-methyloxan-3-yl] acetate
• CAS: 418764-42-8
• 化学式: C₄₄H₅₆O₁₅
• 分子量: 824.92
• InChiKey: QXBMBALXOSCJAX-YOTIOHDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  154
• 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)-3,6-di-O-p-methoxybenzyl-4-O-methyl-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 allyl (2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->2)-3,6-di-O-acetyl-4-O-methyl-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：

  S-ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 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 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 53.0h， 生成 allyl (3,4-di-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-(1->2)-3,6-di-O-p-methoxybenzyl-4-O-methyl-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