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-glucopyranose | 114853-30-4

• 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)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose
• 英文别名: 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-glucopyranose；O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-<(2,3,6-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)>-6-O-benzyl-2-deoxy-2-phtalimido-D-glucopyranose
• CAS: 114853-30-4
• 化学式: C₆₂H₆₇NO₂₀
• 分子量: 1146.21
• InChiKey: VFGANCJMYMAQRD-YZZZWPMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  83.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  245.88
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  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-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以67.1%的产率得到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：

  X半抗原，III3Fucα-nLc4Cer的全合成

  摘要：

  摘要O-β-d-吡喃半乳糖基-（1→4）-O-[α-1-呋喃核糖基-（1→3）]-O-（2-乙酰氨基-2-脱氧-β-d-古豆核糖基的全合成）-（1→3）-O-β-d-吡喃并吡喃糖基-（1→4）-O-β-d-吡喃吡喃糖基-（1→1）-2- N-四十四烷酰基-（2 S，3 R，4通过使用关键的糖基供体O-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-（1→4）-O-[2,3， 4-三-O-乙酰基-α-1-呋喃核糖基）-（1→3）]-O-（2-乙酰氨基-6-O-乙酰基-2-脱氧-β-d-吡喃葡萄糖基）-（1→3 ）-O-（2,4,6-三-O-乙酰基-β-d-吡喃半乳糖基）-（1→4）-2,3,6-三-O-乙酰基-α-d-吡喃葡萄糖基三氯乙酰亚氨酸盐和氟化物，以及关键的糖基受体3- O-苯甲酰基-2- N-四cosanoyl-（2 S，3 R，4 E）-鞘氨醇，以明确的方式。

  DOI：

  10.1016/0008-6215(87)80279-3
• 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)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 硝酸铵 、 ammonium and cerium nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以92%的产率得到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-glucopyranose
  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