methyl 2,3-di-O-benzoyl-α-D-mannopyranosyl-(1-> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside | 666848-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-α-D-mannopyranosyl-(1-> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside
• 英文别名: methyl 2,3-di-O-benzoyl-α-D-mannopyranosyl-(1→4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside；Bz(-2)[Bz(-3)]Man(a1-4)[Bz(-3)][Bz(-6)]a-GlcNAc1Me；[(2R,3S,4R,5R,6S)-5-acetamido-4-benzoyloxy-3-[(2R,3S,4S,5R,6R)-3,4-dibenzoyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 666848-66-4
• 化学式: C₄₃H₄₃NO₁₅
• 分子量: 813.812
• InChiKey: BPTCVHNVFFNBML-YVBMFJCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  212
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-α-D-mannopyranosyl-(1-> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到methyl α-D-mannopyranosyl-(1→ 4)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases

  摘要：

  合成了一种含有四个糖基磷脂酰肌醇的碎片，以模拟酿酒酵母的原型核心特征。这种方法的显著特点在于使用简单的糖基化和保护基技术迅速获得各种α-1,2-和α-1,6-甘露糖基和α-1,4-糖基连接。使用1D和2D-J-解析NMR光谱验证了新连接的α-构型。本研究获得的四糖基物质对于研究真菌细胞壁糖蛋白交联和转糖酶酶类的抗真菌药物开发非常有用。

  DOI：

  10.1055/a-1523-1638
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 、 溶剂黄146 、 乙酰氯 、 原甲酸三乙酯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.0h， 生成 methyl 2,3-di-O-benzoyl-α-D-mannopyranosyl-(1-> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus

  摘要：

  Two oligosaccharides, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(l --> 4)-alpha-D-GlcpNAc (I) and alpha-D-Manp-(1 --> 3)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 4)-alpha-D-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from S. cerevesiae and A. fumigatus were synthesized as their methyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 6-O-selective glycosylation of methyl 2,3-di-O-benzoyl-alpha-D-mannopyranosyl-(l --> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (8) with 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2) -3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9), followed by benzoylation, deacetylation, and mannosylation, and then by deprotection. The hexasaccharide (II) was obtained via condensation of allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(l --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (17) with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (16), followed by deallylation, trichloroacetimidation, and coupling with acceptor (8), and finally by deprotection. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.09.030