Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(b1-4)][Bn(-6)]GlcNAc(a)-O-Bn | 136543-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(b1-4)][Bn(-6)]GlcNAc(a)-O-Bn
• 英文别名: N-[(2S,3R,4R,5S,6R)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 136543-98-1
• 化学式: C₆₂H₇₁NO₁₅
• 分子量: 1070.24
• InChiKey: WMIGZKYFJDJDAO-RLYWENORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  78
• 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：
  191
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(b1-4)][Bn(-6)]GlcNAc(a)-O-Bn 、 二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯 生成
  参考文献：
  名称：

  An Economical Synthesis of Lewis X, Sialyl Lewis X and Their α-Galactosyl Analogues

  摘要：

  Economical syntheses of the Lewis X trisaccharide 8 and sialyl Lewis X tetrasaccharide 18 epitopes and the syntheses of the alpha-galactosyl epimers 9 and 20 of these structures are described. Thioglycosides 2, 5, 11 and 15 were used as glycosyl donors to construct the desired compounds in a stepwise manner in dimethyl(methylthio)sulphonium triflate promoted couplings. Benzyl 3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-acetamido-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside (4) was a key structure in these syntheses, and was synthesised in multi-gram scale.

  DOI：

  10.1080/07328309708005732
• 作为产物：
  描述：

  2,3,4-三-O-苄基-L-吡喃岩藻糖基氟化物 在 4 A molecular sieve 、 sodium methylate 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 5.0h， 生成 Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(b1-4)][Bn(-6)]GlcNAc(a)-O-Bn
  参考文献：
  名称：

  唾液酸化的乐立体控制合成X，寡糖结合配体到ELAM-1（唾液酸= Ñ -acetylneuramin）

  摘要：

  唾液酸勒X 1寡糖结合配体到ELAM-1是由积木合成2 - 5经由设有一个相邻PHS团作为辅助的原理，以促进和立体化学控制期望的糖苷键的形成在目标上的短路线分子。

  DOI：

  10.1039/c39910000870

文献信息

• An Economical Synthesis of Lewis X, Sialyl Lewis X and Their α-Galactosyl Analogues
  作者：Gyula Dekany、Karen Wright、Istvan Toth

  DOI：10.1080/07328309708005732

  日期：1997.9

  Economical syntheses of the Lewis X trisaccharide 8 and sialyl Lewis X tetrasaccharide 18 epitopes and the syntheses of the alpha-galactosyl epimers 9 and 20 of these structures are described. Thioglycosides 2, 5, 11 and 15 were used as glycosyl donors to construct the desired compounds in a stepwise manner in dimethyl(methylthio)sulphonium triflate promoted couplings. Benzyl 3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-2-acetamido-6-O-benzyl-2-deoxy-alpha-D-glucopyranoside (4) was a key structure in these syntheses, and was synthesised in multi-gram scale.
• Stereocontrolled synthesis of sialyl Lex, the oligosaccharide binding ligand to ELAM-1 (sialyl =N-acetylneuramin)
  作者：K. C. Nicolaou、C. W. Hummel、N. J. Bockovich、C.-H. Wong

  DOI：10.1039/c39910000870

  日期：——

  Sialyl Lex1 the oligosaccharide binding ligand to ELAM-1 is synthesized from building blocks 2–5via a short route featuring the principle of a neighbouring PhS group as an auxiliary to facilitate and stereochemically control the formation of the desired glycoside bond in the target molecule.

  唾液酸勒X 1寡糖结合配体到ELAM-1是由积木合成2 - 5经由设有一个相邻PHS团作为辅助的原理，以促进和立体化学控制期望的糖苷键的形成在目标上的短路线分子。