p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 220449-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4R,5S,6R)-5-hydroxy-2-[(4-methoxyphenyl)methoxy]-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 220449-95-6
• 化学式: C₅₆H₅₇NO₁₂
• 分子量: 936.068
• InChiKey: BBPQSTILHNJJAV-WPILKZRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  69
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 硝酸铵 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 ammonium and cerium nitrate 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.08h， 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)]-6-O-benzyl-2-deoxy-2-phthalimido-β-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
• 作为产物：
  描述：

  p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 盐酸 、 3 A molecular sieve 、 四丁基溴化铵 、 sodium cyanoborohydride 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.75h， 生成 p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-6-O-benzyl-2-deoxy-2-phthalimido-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

文献信息

• Synthesis of 3E- And 6E-Monosulfated and 3E,6E-Disulfated Lewis X Pentasaccharides, Candidate Ligands for Human L-Selectin
  作者：André Lubineau、Jocelyne Alais、Remy Lemoine

  DOI：10.1080/07328300008544072

  日期：2000.1

  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.