5-methoxycarbonylpentyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-3,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-β-D-mannopyranoside | 1011529-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxycarbonylpentyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-3,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-β-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5S,6R)-3,4-dibenzoyloxy-6-(6-methoxy-6-oxohexoxy)-5-[(2S,3R,4S,5R)-3,4,5-tribenzoyloxyoxan-2-yl]oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 1011529-25-1
• 化学式: C₈₇H₇₈O₂₆
• 分子量: 1539.56
• InChiKey: LFRVNALOQJEVEK-CDXVDWTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  113
• 可旋转键数：
  41
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  318
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylpentyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-3,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-β-D-mannopyranoside 在 甲醇 、 sodium 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以98%的产率得到5-carboxypentyl 2-O-(β-D-xylopyranosyl)-6-O-(α-D-mannopyranosyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of cross-reactive carbohydrate determinants fragments as tools for in vitro allergy diagnosis

  摘要：

  Four biotinylated tri and tetrasaccharide fragments of plant and invertebrate N-glycans were synthesized using methyl tert-butyl phenyl (MBP) thioglycosides donors in order to evaluate their involvement in cross-allergies as cross-reactive carbohydrate determinants (CCDs). Various levels of reactivity to anti-bee and anti-HRP antibodies and with sera from allergic patients were observed when the conjugates were coated on streptavidin microplates. The results showed the potential utility of these xylosylated and fucosylated oligosaccharide fragments in determining CCD antibody epitopes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.001
• 作为产物：
  描述：

  (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-benzoyl-1-thio-D-mannopyranoside 、 5-methoxycarbonylpentyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-3,4-di-O-benzoyl-β-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以98%的产率得到5-methoxycarbonylpentyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-3,4-di-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-β-D-mannopyranoside
  参考文献：
  名称：

  用于无味合成与食物过敏原有关的MUXF 3 N-聚糖片段的新型硫糖苷衍生物

  摘要：

  硫糖苷是用于复杂寡糖构建的有价值的工具。由于它们的稳定性和结晶性，它们具有宝贵的优势。然而，它们的主要缺点是用作前体的硫醇的排斥性气味，通常是其毒性，例如在通常使用的硫酚和硫代乙醇的情况下。使用可商购的甲基叔丁基苯基硫醇（MbpSH）避免了这些问题，并且与硫糖苷供体的克规模合成相容。在本文中，我们描述了Mbp硫代糖苷是无味寡糖合成的有用且便捷的前体，并且我们进一步证明了它们的多功能性，证明它们在N聚糖中发现的大多数糖苷键的构建中都得到了证明。

  DOI：

  10.1016/j.tet.2007.11.002

文献信息

• New thioglycoside derivatives for use in odourless synthesis of MUXF3 N-glycan fragments related to food allergens
  作者：Mayeul Collot、Julie Savreux、Jean-Maurice Mallet

  DOI：10.1016/j.tet.2007.11.002

  日期：2008.2

  of thiols utilised as precursors and, often, their toxicity such as in case of the commonly employed thiophenol and thioethanol. The use of commercially available methyl tert-butyl phenyl thiol (MbpSH) avoids these problems and is compatible with gram scale synthesis of thioglycoside donors. In this paper, we describe that Mbp thioglycosides are useful and convenient precursors for odourless oligosaccharide

  硫糖苷是用于复杂寡糖构建的有价值的工具。由于它们的稳定性和结晶性，它们具有宝贵的优势。然而，它们的主要缺点是用作前体的硫醇的排斥性气味，通常是其毒性，例如在通常使用的硫酚和硫代乙醇的情况下。使用可商购的甲基叔丁基苯基硫醇（MbpSH）避免了这些问题，并且与硫糖苷供体的克规模合成相容。在本文中，我们描述了Mbp硫代糖苷是无味寡糖合成的有用且便捷的前体，并且我们进一步证明了它们的多功能性，证明它们在N聚糖中发现的大多数糖苷键的构建中都得到了证明。
• Synthesis of cross-reactive carbohydrate determinants fragments as tools for in vitro allergy diagnosis
  作者：Mayeul Collot、Iain B.H. Wilson、Merima Bublin、Karin Hoffmann-Sommergruber、Jean-Maurice Mallet

  DOI：10.1016/j.bmc.2010.12.001

  日期：2011.2

  Four biotinylated tri and tetrasaccharide fragments of plant and invertebrate N-glycans were synthesized using methyl tert-butyl phenyl (MBP) thioglycosides donors in order to evaluate their involvement in cross-allergies as cross-reactive carbohydrate determinants (CCDs). Various levels of reactivity to anti-bee and anti-HRP antibodies and with sera from allergic patients were observed when the conjugates were coated on streptavidin microplates. The results showed the potential utility of these xylosylated and fucosylated oligosaccharide fragments in determining CCD antibody epitopes. (C) 2010 Elsevier Ltd. All rights reserved.