4,6-di-O-acetyl-2,3-di-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate | 618106-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-di-O-acetyl-2,3-di-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)]Man4Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl] benzoate
• CAS: 618106-51-7
• 化学式: C₂₆H₂₄Cl₃NO₁₀
• 分子量: 616.836
• InChiKey: LTDWAXGDCNBSTD-UVSNUMOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,6-di-O-acetyl-2,3-di-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,2-bis[2,3-di-O-benzoyl-α-D-mannopyranosyloxy]ethane
  参考文献：
  名称：

  Concise syntheses of β-GlcNAcp-(1→6)-α-Manp-(1→6)-Manp and its dimer, and β-GlcNAcp-(1→2)-α-Manp-(1→6)-Manp

  摘要：

  beta-D-GlcNAcp-(1-->6)-alpha-D-Manp-(1-->6)-D-Manp and beta-D-GlcNAcp-(1-->2)-alpha-D-Manp-(1-->6)-D-Manp were synthesized as their methyl glycosides in a regio- and stereoselective way, whereas an ethylene glycol-coupled dimer of the former was prepared in a convergent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00570-6
• 作为产物：
  描述：

  在 甲醇 、 硫酸 、 氨 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 4,6-di-O-acetyl-2,3-di-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Concise syntheses of β-GlcNAcp-(1→6)-α-Manp-(1→6)-Manp and its dimer, and β-GlcNAcp-(1→2)-α-Manp-(1→6)-Manp

  摘要：

  beta-D-GlcNAcp-(1-->6)-alpha-D-Manp-(1-->6)-D-Manp and beta-D-GlcNAcp-(1-->2)-alpha-D-Manp-(1-->6)-D-Manp were synthesized as their methyl glycosides in a regio- and stereoselective way, whereas an ethylene glycol-coupled dimer of the former was prepared in a convergent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00570-6

文献信息

• Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases
  作者：Tyson F. Belz

  DOI：10.1055/a-1523-1638

  日期：2021.12

  A glycophosphatidylinositol tetrasaccharide fragment was synthesized to mimic the core features of primary model, that of Saccharomyces cerevisiae. The salient feature of this approach is centered on the quick access to various α-1,2- and α-1,6-mannosyl and α-1,4-glycosyl linkages by using simple glycosylation and protective-group techniques. 1D and 2D-J-resolved NMR spectroscopy was used to verify the α-configuration of the new linkages. The tetrasaccharides obtained in this work are useful for examining fungal cell-wall glycoprotein cross-linking by transglycosidase enzymes for antifungal drug development.

  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。

• Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.carres.2003.09.030

  日期：2004.1

  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.