Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(a1-4)][Bn(-6)]GlcNAc(a)-O-Bn | 196957-69-4

• 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(a1-4)][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-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 196957-69-4
• 化学式: C₆₂H₇₁NO₁₅
• 分子量: 1070.24
• InChiKey: WMIGZKYFJDJDAO-GVENAGITSA-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：

  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 、 Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(a1-4)][Bn(-6)]GlcNAc(a)-O-Bn 在 DMTST 作用下， 生成 benzyl O-[6-O-benzyl-3-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranosyl]-(1->4)-O-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-2-acetamido-6-O-benzyl-2-deoxy-α-D-glucop...
  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：

  在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以2.29 g的产率得到Bn(-2)[Bn(-3)][Bn(-4)]Fuc(a1-3)[Bn(-6)Gal(a1-4)][Bn(-6)]GlcNAc(a)-O-Bn
  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