4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine | 294623-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine
• 英文别名: benzyl (2S,3R,4R)-2-ethyl-3-hydroxy-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxypyrrolidine-1-carboxylate
• CAS: 294623-65-7
• 化学式: C₄₁H₄₇NO₈
• 分子量: 681.826
• InChiKey: CWSUTCCXBGEKNI-RECBNXBFSA-N

物化性质

• 沸点：
  771.2±60.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1,2-O-[1-exo-(2S,3R,4R)-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-benzyloxycarbonyl-2-ethyl-3,4-dihydroxy-3-yl-pyrrolidine)ethylidene]-β-D-galactopyranose
  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 The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12.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：

  methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside 在 palladium on activated charcoal 吡啶 、 咪唑 、 盐酸 、 二叔丁基过氧化物 、 氢气 、 碘 、 silver perchlorate 、 sodium cyanoborohydride 、 sodium carbonate 、 tin(IV) oxide 、 三苯基膦 、 锌 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 82.75h， 生成 4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(2S,3R,4R)-1-benzyloxycarbonyl-3,4-dihydroxy-2-ethylpyrrolidine
  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