2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-D-galactono-1,4-lactone | 1319734-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-D-galactono-1,4-lactone
• 英文别名: [(3R,4S,5S)-4-[(2R,3R,4S,5S)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3,4-bis(phenylmethoxy)oxolan-2-yl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl] benzoate
• CAS: 1319734-82-1
• 化学式: C₅₀H₅₂O₁₂
• 分子量: 844.956
• InChiKey: DRWPKHPUUJVNKU-LEKFWEFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  62
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl trichloroacetimidate 、 2-O-benzoyl-5,6-O-isopropylidene-D-galactono-1,4-lactone 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以35%的产率得到2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-D-galactono-1,4-lactone
  参考文献：
  名称：

  Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation

  摘要：

  Glycosylation studies for the construction of 1,2-cis alpha-linkages with O-(2,3,5,6-tetra-O-benzyl-beta-D-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including D-mannosyl and L-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH2Cl2, Et2O, and acetonitrile as solvents. A non-participating solvent such as CH2Cl2 at 78 degrees C, favored the alpha-D-configuration. In contrast, acetonitrile strongly favored the beta-D-configuration, whereas no selectivities were observed with Et2O. The use of thiophene as an additive did not enhance the alpha-D-selectivity as in the pyranose counterpart. Although selectivities strongly depended on the acceptor, trichloroacetimidate 1 constitutes a valuable donor for the synthesis of alpha-D-Galf-(1 -> 2)-L-Rha and alpha-D-Galf-(1 -> 6)-D-Man. As these motifs are present in pathogenic microorganisms, these procedures described here are useful for the straightforward synthesis of natural oligosaccharides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.005

文献信息

• Influence of the solvent in low temperature glycosylations with O-(2,3,5,6-tetra-O-benzyl-β-d-galactofuranosyl) trichloroacetimidate for 1,2-cis α-d-galactofuranosylation
  作者：Gabriel Gola、Mariano J. Tilve、Carola Gallo-Rodriguez

  DOI：10.1016/j.carres.2011.04.005

  日期：2011.9

  Glycosylation studies for the construction of 1,2-cis alpha-linkages with O-(2,3,5,6-tetra-O-benzyl-beta-D-galactofuranosyl) trichloroacetimidate (1) and several acceptors, including D-mannosyl and L-rhamnosyl derivatives were performed. The reactions were conducted at low temperatures using CH2Cl2, Et2O, and acetonitrile as solvents. A non-participating solvent such as CH2Cl2 at 78 degrees C, favored the alpha-D-configuration. In contrast, acetonitrile strongly favored the beta-D-configuration, whereas no selectivities were observed with Et2O. The use of thiophene as an additive did not enhance the alpha-D-selectivity as in the pyranose counterpart. Although selectivities strongly depended on the acceptor, trichloroacetimidate 1 constitutes a valuable donor for the synthesis of alpha-D-Galf-(1 -> 2)-L-Rha and alpha-D-Galf-(1 -> 6)-D-Man. As these motifs are present in pathogenic microorganisms, these procedures described here are useful for the straightforward synthesis of natural oligosaccharides. (C) 2011 Elsevier Ltd. All rights reserved.