methyl 2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside | 1051371-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-5)][Bn(-6)]Galf(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]a-Man1Me；[(2R,3R,4S,5S,6S)-4,5-dibenzoyloxy-2-[[(2S,3R,4S,5S)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3,4-bis(phenylmethoxy)oxolan-2-yl]oxymethyl]-6-methoxyoxan-3-yl] benzoate
• CAS: 1051371-60-8
• 化学式: C₆₂H₆₀O₁₄
• 分子量: 1029.15
• InChiKey: HZKJOQOPRBQXBG-LNTWGFQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  76
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 、 2'-carboxybenzyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 molecular sieve 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,3,5,6-tetra-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 、 methyl 2,3,5,6-tetra-O-benzyl-α-D-galactofuranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  立体选择性α-galactofuranosylation和二-合成和细胞壁多糖的四糖亚基的Talaromyces黄曲霉

  摘要：

  已经建立了使用2'-羧基苄基糖苷作为半乳糖基供体的立体选择性α-半呋喃糖基化。半乳糖基供体上的四苄基保护基对于仲醇受体的α-半乳糖基化至关重要。本方法已成功地应用于合成了Talaromyces flavus细胞壁多糖的二糖和四糖亚基。

  DOI：

  10.1016/j.tetlet.2008.05.118

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.
• Stereoselective α-galactofuranosylation and synthesis of di- and tetrasaccharide subunits of cell wall polysaccharides of Talaromyces flavus
  作者：Ju Yuel Baek、Yong Jae Joo、Kwan Soo Kim

  DOI：10.1016/j.tetlet.2008.05.118

  日期：2008.8

  ve group on the galactosyl donor was essential for the α-galactosylation of secondary alcohol acceptors. The present method was successfully applied to the synthesis of di- and tetrasaccharide subunits of cell wall polysaccharides of Talaromyces flavus.

  已经建立了使用2'-羧基苄基糖苷作为半乳糖基供体的立体选择性α-半呋喃糖基化。半乳糖基供体上的四苄基保护基对于仲醇受体的α-半乳糖基化至关重要。本方法已成功地应用于合成了Talaromyces flavus细胞壁多糖的二糖和四糖亚基。