O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate | 220449-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Gal2Ac3Ac4Ac6Ac(b1-4)][Bn(-6)]GlcNAc(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 220449-99-0
• 化学式: C₅₈H₆₇Cl₃N₂O₁₉
• 分子量: 1202.53
• InChiKey: TYROHDBSMHZSSJ-OGYXRPOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  82
• 可旋转键数：
  29
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  250
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 、 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 15.0h， 以24%的产率得到benzyl O-(β-D-galactopyranosyl)-(1-> 4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)]-O-(2-acetamido-6-O-benzyl-2-O-deoxy-β-D-glucopyranosyl)-(1-> 3)-O-(2,6-di-O-O-benzyl-β-D-galactopyranosyl)-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3E- And 6E-Monosulfated and 3E,6E-Disulfated Lewis X Pentasaccharides, Candidate Ligands for Human L-Selectin

  摘要：

  Condensation of perbenzyl fucosyl bromide 4 with the known 2-acetamido derivative 1 and with the 2-phthalimido analog 3 gave, respectively, disaccharides 5 and 6 which, after reductive opening of the benzylidene group were glycosylated using peracetylated galactose trichloroacetimidate to give trisaccharides 10 and 11. After removal of the anomeric p-methoxybenzyl group and subsequent activation as the trichloroacetimidate, condensation onto the known lactose derivative 16 afforded protected pentasaccharides 18 and 17 in 24 and 70% yields, respectively. Compound 17 was transformed into 18 by a conventional method in 77% yield making the phthalimido route overall more attractive. The terminal galactose was then selectively deprotected and sulfated at the 3e, 6e and both 3e,6e positions to give the title compounds after complete deprotection.

  DOI：

  10.1080/07328300008544072
• 作为产物：
  描述：

  p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 硝酸铵 、 ammonium and cerium nitrate 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.08h， 生成 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of 3E- And 6E-Monosulfated and 3E,6E-Disulfated Lewis X Pentasaccharides, Candidate Ligands for Human L-Selectin

  摘要：

  Condensation of perbenzyl fucosyl bromide 4 with the known 2-acetamido derivative 1 and with the 2-phthalimido analog 3 gave, respectively, disaccharides 5 and 6 which, after reductive opening of the benzylidene group were glycosylated using peracetylated galactose trichloroacetimidate to give trisaccharides 10 and 11. After removal of the anomeric p-methoxybenzyl group and subsequent activation as the trichloroacetimidate, condensation onto the known lactose derivative 16 afforded protected pentasaccharides 18 and 17 in 24 and 70% yields, respectively. Compound 17 was transformed into 18 by a conventional method in 77% yield making the phthalimido route overall more attractive. The terminal galactose was then selectively deprotected and sulfated at the 3e, 6e and both 3e,6e positions to give the title compounds after complete deprotection.

  DOI：

  10.1080/07328300008544072