2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->5)]-2-O-acetyl-3-O-benzyl-β-D-galactofuranosyl trichloroacetimidate | 849355-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->5)]-2-O-acetyl-3-O-benzyl-β-D-galactofuranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)]Galf6Ac(b1-5)[Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-6)][Bn(-3)]Galf2Ac(b)-O-C(NH)CCl3；[(2S,3S,4R,5R)-2-[(1R)-2-acetyloxy-1-benzoyloxyethyl]-5-[(1R)-1-[(2S,3S,4R,5S)-4-acetyloxy-3-phenylmethoxy-5-(2,2,2-trichloroethanimidoyl)oxyoxolan-2-yl]-2-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyethoxy]-4-benzoyloxyoxolan-3-yl] benzoate
• CAS: 849355-86-8
• 化学式: C₈₀H₇₈Cl₃NO₂₁
• 分子量: 1495.85
• InChiKey: GCECZIIELAIVMW-XTCOPMMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  105
• 可旋转键数：
  39
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  257
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->5)]-2-O-acetyl-3-O-benzyl-β-D-galactofuranosyl trichloroacetimidate 、 十二烷醇 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到dodecyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->5)]-2-O-acetyl-3-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  First synthesis of 5,6-branched galacto-hexasaccharide, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016

  摘要：

  alpha-D-Galactopyranosyl-(1 --> 6)-[beta-D-galactofuranosyl-(1 --> 5)]-beta-D-galactofuranosyl-(1 --> 6)-beta-D-galactofuranosyl-(1 --> 5)-[alpha-D -galactopyranosyl-(1 --> 6)]-beta-D-galactofuranose, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016, has been synthesized as its dodecyl glycoside 2 by coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranosyl trichloroacetimidate 14 with dodecyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranoside 16. The trisaccharide trichloroacetimidate donor 14 and trisaccharide acceptor 16 were regiospecifically prepared by employing 3-O-benzyl-1,2-O-isopropylidene-alpha-D-galactofuranose 4 as the glycosyl acceptor, and isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside 5 and 6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate 9 as glycosyl donors. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.014
• 作为产物：
  描述：

  Bz(-2)[Bz(-3)][Bz(-5)]Galf6Ac(b1-5)[Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-6)][Bn(-3)]b-Galf2Ac 、 三氯乙腈 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以2.6 g的产率得到2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-β-D-galactofuranosyl-(1->5)]-2-O-acetyl-3-O-benzyl-β-D-galactofuranosyl trichloroacetimidate
  参考文献：
  名称：

  First synthesis of 5,6-branched galacto-hexasaccharide, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016

  摘要：

  alpha-D-Galactopyranosyl-(1 --> 6)-[beta-D-galactofuranosyl-(1 --> 5)]-beta-D-galactofuranosyl-(1 --> 6)-beta-D-galactofuranosyl-(1 --> 5)-[alpha-D -galactopyranosyl-(1 --> 6)]-beta-D-galactofuranose, the dimer of the trisaccharide repeating unit of the cell-wall galactans of Bifidobacterium catenulatum YIT 4016, has been synthesized as its dodecyl glycoside 2 by coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranosyl trichloroacetimidate 14 with dodecyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1 --> 6)-[2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)]-2-O-acetyl-3-O-benzyl-beta-D-galactofuranoside 16. The trisaccharide trichloroacetimidate donor 14 and trisaccharide acceptor 16 were regiospecifically prepared by employing 3-O-benzyl-1,2-O-isopropylidene-alpha-D-galactofuranose 4 as the glycosyl acceptor, and isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside 5 and 6-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate 9 as glycosyl donors. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.014