methoxyethyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(3-O-carbobenzyloxymethyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 1139754-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methoxyethyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(3-O-carbobenzyloxymethyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS: 1139754-23-6
• 化学式: C₄₄H₅₈O₁₈
• 分子量: 874.934
• InChiKey: SKXODKJEWRQOOB-IKUGUACVSA-N

物化性质

• 沸点：
  1003.1±65.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  62.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  239.98
• 氢给体数：
  6.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methoxyethyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(3-O-carbobenzyloxymethyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到methoxyethyl 3-O-(α-L-fucopyranosyl)-4-O-(3-O-carbobenzyloxymethyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Regioselective synthesis of a glycomimetic trisaccharide of Sialyl Lewis (sLex)

  摘要：

  Sialyl Lewis (sLe(x)) is the smallest naturally occurring carbohydrate ligand that binds to E-Selectin on the activated endothelium. We report here the total synthesis of acetic acid-sLe(x) analog (12), for testing as a therapeutic agent. Methoxyethyl 4-O-(3,4-O-isopropylidene-beta-D-galactopyranosyl)-beta-D-glucopyranoside (3) was prepared starting from the methoxyethyl-beta-D-lactoside (2), which was selectively benzoylated to give the methoxyethyl 2,6-di-O-benzoyl-4-beta-(2,6-di-O-benzoyl-3,4-0-isopropylidene-beta-D-galactopyranosyl)-beta-D-glucopyranoside (4). Glycosylation of acceptor 4 with methyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside (5) in the presence of cupric bromide and tetrabutylammonium bromide afforded the corresponding methoxyethyl 2,6-di-O-benzyl-3-beta-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-4-0-(2,6-di-O-benzyl-3,4-O-isopropylidene-beta-D-galactopyranosyl)-P-D-glucopyranoside (6). Selective removal of the 4 '',6 ''-O-isopropylidene group from 6 gave the deprotected trisaccharide 7. The regioselective esterification of O-3 '' of trisaccharide 8 (obtained from the dibutylstannylene derivative of 7) with benzyl-2-bromoacetate and tetrabutylammonium bromide afforded the 3 ''-O-carbobenzyloxymethyl trisaccharide derivative 9, which on saponification and hydrogenolysis with palladium-charcoal afforded the target trisaccharide 12 glycomimetic of Sialyl Lewis (sLe(x)) trisaccharide omitting the sialic acid moiety.

  DOI：

  10.1016/j.carres.2008.11.019
• 作为产物：
  描述：

  methoxyethyl 2,6-di-O-benzoyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(2,6-di-O-benzoyl-3-O-carbobenzyloxymethyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 甲醇 、 sodium 作用下， 反应 2.0h， 生成 methoxyethyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(3-O-carbobenzyloxymethyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Regioselective synthesis of a glycomimetic trisaccharide of Sialyl Lewis (sLex)

  摘要：

  Sialyl Lewis (sLe(x)) is the smallest naturally occurring carbohydrate ligand that binds to E-Selectin on the activated endothelium. We report here the total synthesis of acetic acid-sLe(x) analog (12), for testing as a therapeutic agent. Methoxyethyl 4-O-(3,4-O-isopropylidene-beta-D-galactopyranosyl)-beta-D-glucopyranoside (3) was prepared starting from the methoxyethyl-beta-D-lactoside (2), which was selectively benzoylated to give the methoxyethyl 2,6-di-O-benzoyl-4-beta-(2,6-di-O-benzoyl-3,4-0-isopropylidene-beta-D-galactopyranosyl)-beta-D-glucopyranoside (4). Glycosylation of acceptor 4 with methyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside (5) in the presence of cupric bromide and tetrabutylammonium bromide afforded the corresponding methoxyethyl 2,6-di-O-benzyl-3-beta-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-4-0-(2,6-di-O-benzyl-3,4-O-isopropylidene-beta-D-galactopyranosyl)-P-D-glucopyranoside (6). Selective removal of the 4 '',6 ''-O-isopropylidene group from 6 gave the deprotected trisaccharide 7. The regioselective esterification of O-3 '' of trisaccharide 8 (obtained from the dibutylstannylene derivative of 7) with benzyl-2-bromoacetate and tetrabutylammonium bromide afforded the 3 ''-O-carbobenzyloxymethyl trisaccharide derivative 9, which on saponification and hydrogenolysis with palladium-charcoal afforded the target trisaccharide 12 glycomimetic of Sialyl Lewis (sLe(x)) trisaccharide omitting the sialic acid moiety.

  DOI：

  10.1016/j.carres.2008.11.019