2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate | 583043-08-7

• 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-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside trichloroacetimidate；2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate；2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl) trichloroacetimidate；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3,4-dibenzoyloxy-5-[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 583043-08-7
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: OQWAWUFWMZLFLW-NLMRDXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 、 methyl 2,3-di-O-benzoyl-α-D-mannopyranosyl-(1-> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以45%的产率得到
  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：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  First syntheses of d-mannose penta- and decasaccharides, the repeating unit and its dimer of the cell-wall mannan of Candida kefyr IFO 0586

  摘要：

  alpha-D-Mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose and alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)]-alpha-D-marmopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose, the repeating unit and its dimer of the cell wall mannan of the pathogenic yeast Candida kefyr IFO 0586, have been efficiently synthesized via their allyl glycosides by using allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside, allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside, and allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside as synthons. The blocked pentasaccharide was regio- and stereoselectively prepared by coupling of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, and then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate in a one-pot manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00216-7

文献信息

• Straightforward synthesis of Man₉, the relevant epitope of the high-mannose oligosaccharide
  作者：Javier Ramos-Soriano、M. Carmen de la Fuente、Noelia de la Cruz、Rute C. Figueiredo、Javier Rojo、José J. Reina

  DOI：10.1039/c7ob02286g

  日期：——

  well-defined structures in reasonable amounts. The synthesis of these complex branched oligosaccharides is not trivial and few syntheses are reported in the literature with several synthetic and purification steps and low overall yields. In this work, we described a very efficient synthetic alternative to access this relevant Man9 epitope in a very straightforward manner.

  高甘露糖寡糖（或其对应的Man 9表位）是病原体包膜糖蛋白中存在的最丰富的结构。这些聚糖在几种病原体的发病机理以及与免疫系统的通讯中起关键作用。了解这些聚糖的作用机理需要以合理的量获得纯净的和化学上明确定义的结构。这些复杂的支链低聚糖的合成并非易事，文献报道的合成很少，具有几个合成和纯化步骤，总收率低。在这项工作中，我们描述了一种非常有效的合成替代品，可以以非常简单的方式访问此相关的Man 9表位。
• High‐Mannose Oligosaccharide Hemimimetics that Recapitulate the Conformation and Binding Mode to Concanavalin A, DC‐SIGN and Langerin
  作者：Irene Herrera‐González、Manuel González‐Cuesta、Michel Thépaut、Eugénie Laigre、David Goyard、Javier Rojo、José M. García Fernández、Franck Fieschi、Olivier Renaudet、Pedro M. Nieto、Carmen Ortiz Mellet

  DOI：10.1002/chem.202303041

  日期：2024.1.8

  The “carbohydrate chemical mimicry” of sp2-iminosugars enables the synthesis of high-mannose-type oligosaccharide analogs whose solution and lectin bound conformations match those of the natural partners. Upon multivalent presentation, enhanced affinities towards ConA, DC-SIGN and langerin are achieved, with distinct selectivity profiles.

  sp 2 -亚氨基糖的“碳水化合物化学模拟”能够合成高甘露糖型寡糖类似物，其溶液和凝集素结合构象与天然伙伴相匹配。多价呈递后，可增强对 ConA、DC-SIGN 和 langerin 的亲和力，并具有不同的选择性特征。
• Convergent synthesis of a galactofuranosylated mannan, the repeating unit of Trichophyton mentagrophytes IFO 5466 and Trichophyton rubrum IFO 5467
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.tetasy.2004.03.041

  日期：2004.5

  An undecasaccharide repeating unit of the polysaccharide of Trichophyton mentagrophytes IFO 5466 and Trichophyton rubrum IFO 5467, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-[beta-D-Galf-(1 --> 3)]-alpha-D-Manp-(1 --> 2)-[beta-D-Galf-(1 --> 3)]-alpha-D-Manp(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 2)-[beta-D-Galf-(1 --> 3)]-Manp was synthesized as its allyl glycoside by coupling of a octasaccharide trichloroacetimidate donor 19 with a trisaccharide acceptor 28. The donor 19 and 28 were obtained with allyl 3-O-acetyl-2-O-betizoyl-alpha-D-mannopyranoside 2, allyl 3-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside 9, allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2)-3,4,6-tri-O-belizoyl-alpha-D-mannopyranoside 13, 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate 26 and 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuraliosyl trichloroacetimidate 16 as the key synthons by appropriate combination through simple transformation. (C) 2004 Elsevier Ltd. All rights reserved.
• 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。

• First syntheses of d-mannose penta- and decasaccharides, the repeating unit and its dimer of the cell-wall mannan of Candida kefyr IFO 0586
  作者：Ying Xing、Jun Ning

  DOI：10.1016/s0957-4166(03)00216-7

  日期：2003.5

  alpha-D-Mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose and alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)]-alpha-D-marmopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose, the repeating unit and its dimer of the cell wall mannan of the pathogenic yeast Candida kefyr IFO 0586, have been efficiently synthesized via their allyl glycosides by using allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside, allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside, and allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside as synthons. The blocked pentasaccharide was regio- and stereoselectively prepared by coupling of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, and then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate in a one-pot manner. (C) 2003 Elsevier Science Ltd. All rights reserved.