4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine | 294623-68-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine
• CAS: 294623-68-0
• 化学式: C₇₅H₇₃NO₁₇
• 分子量: 1260.4
• InChiKey: PWRBZMFORPXOFT-GRDIJQQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.95
• 重原子数：
  93.0
• 可旋转键数：
  25.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  199.35
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine 在 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.25h， 生成 Sulfuric acid mono-{(2R,3R,4S,5S,6R)-2-[(2S,3R,4R)-2-ethyl-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-pyrrolidin-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl} ester
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095
• 作为产物：
  描述：

  (3R,4R,5S)-5-ethylpyrrolidine-3,4-diol 在 2,4,6-三甲基吡啶 、 二叔丁基过氧化物 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 silver perchlorate 、 sodium carbonate 、 tin(IV) oxide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 50.5h， 生成 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxypyrrolidine
  参考文献：
  名称：

  Synthesis of A Novel Sialyl Lewis X Analogue Containing A Pyrrolidine in Place ofN-Acetyl Glucosamine

  摘要：

  The synthesis of the new sialyl Lewis X analogue, 4-O-(alpha-L-fucopyranosyl)-3-O-(3-O-sodium sulfonato-beta-D-galactopyranosyl)-(2S,3R, 4R)-2-ethyl-3,4-dihydroxypyrrolidine 2 has been achieved. The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12. This one has been synthezised from the methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-alpha-D-altropyranoside sugar precursor 10 using the Ganem/Bernotas one-pot elimination-reductive amination ring contraction reaction. The (2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 12 obtained was subsequently regioselectively glycosylated, using 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl fluoride and 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl bromide as glycosyl donors. Disaccharide containing pyrrolidine 21 was finally transformed into the target O-sulfated analog 2, after regioselective sulfation and usual deprotection.

  DOI：

  10.1080/07328300008544095