4-methoxyphenyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside) | 219489-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(b1-4)][Bn(-6)]GlcNAc(b)-O-Ph(4-OMe)；N-[(2S,3R,4R,5S,6R)-2-(4-methoxyphenoxy)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 219489-06-2
• 化学式: C₆₂H₇₁NO₁₆
• 分子量: 1086.24
• InChiKey: OCJRJQMPKBPMDU-UZFKTLHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate 、 乙酸酐 、 4-methoxyphenyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside) 生成 4-methoxyphenyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>(1->3)-(2-acetamido-6-O-benzyl-2-deoxy-D-glucopyranoside) 、 4-methoxyphenyl (methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-(4-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-...
  参考文献：
  名称：

  A High Yielding Chemical Synthesis of Sialyl Lewis x Tetrasaccharide and Lewis x Trisaccharide; Examples of Regio- and Stereodifferentiated Glycosylations

  摘要：

  Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-n-glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-beta-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1-->3- and 1-->4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 beta/alpha-mixture of 4-O-linked disaccharides (highly regio- but not stereoselective glycosylation).

  DOI：

  10.1021/jo981203x
• 作为产物：
  描述：

  1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐 在 盐酸 、 甲磺酰溴 、 3 Angstroems MS 、 三氟化硼乙醚 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium cyanoborohydride 、 对甲苯磺酸 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 34.78h， 生成 4-methoxyphenyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)
  参考文献：
  名称：

  A High Yielding Chemical Synthesis of Sialyl Lewis x Tetrasaccharide and Lewis x Trisaccharide; Examples of Regio- and Stereodifferentiated Glycosylations

  摘要：

  Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-n-glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-beta-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1-->3- and 1-->4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 beta/alpha-mixture of 4-O-linked disaccharides (highly regio- but not stereoselective glycosylation).

  DOI：

  10.1021/jo981203x

文献信息

• A High Yielding Chemical Synthesis of Sialyl Lewis x Tetrasaccharide and Lewis x Trisaccharide; Examples of Regio- and Stereodifferentiated Glycosylations
  作者：Ulf Ellervik、Göran Magnusson

  DOI：10.1021/jo981203x

  日期：1998.12.1

  Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-n-glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-beta-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1-->3- and 1-->4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 beta/alpha-mixture of 4-O-linked disaccharides (highly regio- but not stereoselective glycosylation).