methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside | 294623-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside
• 英文别名: [(2S,3S,4R,5S,6S)-2-(iodomethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
• CAS: 294623-62-4
• 化学式: C₂₈H₂₉IO₆
• 分子量: 588.439
• InChiKey: XWQCYYWUGMPASF-KCYOCBRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside 在 palladium on activated charcoal 盐酸 、 二叔丁基过氧化物 、 氢气 、 silver perchlorate 、 sodium cyanoborohydride 、 sodium carbonate 、 tin(IV) oxide 、 锌 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， 反应 64.5h， 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 The N-acetyl glucosamine unit of natural Lewis X has been replaced by a rigid 3R/4R-dihydroxylated pyrrolidine 12.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
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-altropyranoside 在 吡啶 、 咪唑 、 碘 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.25h， 生成 methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-altropyranoside
  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