methoxyethyl 2,6-di-O-benzoyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 1139754-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methoxyethyl 2,6-di-O-benzoyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bz(-2)[Bz(-6)]Gal(b1-4)][Bz(-2)][Bz(-6)]Glc(b)-O-EtOMe；[(2R,3R,4S,5R,6S)-5-benzoyloxy-6-[(2R,3R,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2-methoxyethoxy)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-3-yl]oxy-3,4-dihydroxyoxan-2-yl]methyl benzoate
• CAS: 1139754-19-0
• 化学式: C₇₀H₇₂O₂₀
• 分子量: 1233.33
• InChiKey: XHHKWICFKPGOOV-QCRZXZTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  90
• 可旋转键数：
  31
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  238
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为反应物：
  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-β-D-galactopyranosyl)-β-D-glucopyranoside 在 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  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-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 反应 4.0h， 以86%的产率得到methoxyethyl 2,6-di-O-benzoyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4-O-(2,6-di-O-benzoyl-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

文献信息

• Regioselective synthesis of a glycomimetic trisaccharide of Sialyl Lewis (sLex)
  作者：Sameh E. Soliman、Rafik W. Bassily、Ramadan I. El-Sokkary、Joseph Banoub、Mina A. Nashed

  DOI：10.1016/j.carres.2008.11.019

  日期：2009.2

  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.