2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol | 204068-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol
• 英文别名: (2S,3S,4R,5R,6R)-2-(azidomethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 204068-81-5
• 化学式: C₃₅H₃₇N₃O₅
• 分子量: 579.696
• InChiKey: CGYVFLUMSHWYJL-IVFJIKSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol 在 三乙烯二胺 、 sodium tetrahydroborate 、 (Cl₃CO)2CO 、 nickel dichloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-isocyanomethyl-tetrahydro-pyran
  参考文献：
  名称：

  An Access to Glycoconjugate Libraries through Multicomponent Reactions

  摘要：

  Four-component reactions: The Ugi reaction of four suitably functionalized carbohydrate derivatives (as a per-O-benzylated amine, an aldehyde, a carboxylic acid, and an isocyanide) allow the effective assembly of diverse compound libraries. The complex glycoconjugates formed can be deprotected (see the picture for an example), and the resulting glycomimetics are of high interest for screening purposes.

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3436::aid-anie3436>3.0.co;2-z
• 作为产物：
  描述：

  1-(O-p-toluenesulfonyl)-3,4,5,7-tetra-O-benzyl-2,6-anhydroglucoheptitol 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,6-anhydro-1-azido-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-guloheptitol
  参考文献：
  名称：

  An Access to Glycoconjugate Libraries through Multicomponent Reactions

  摘要：

  Four-component reactions: The Ugi reaction of four suitably functionalized carbohydrate derivatives (as a per-O-benzylated amine, an aldehyde, a carboxylic acid, and an isocyanide) allow the effective assembly of diverse compound libraries. The complex glycoconjugates formed can be deprotected (see the picture for an example), and the resulting glycomimetics are of high interest for screening purposes.

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3436::aid-anie3436>3.0.co;2-z

文献信息

• <i>C</i>-Glycoside Clustering on Calix[4]arene, Adamantane, and Benzene Scaffolds through 1,2,3-Triazole Linkers
  作者：Alessandro Dondoni、Alberto Marra

  DOI：10.1021/jo0607156

  日期：2006.9.1

  A route has been paved toward the preparation of triazole glycocluster libraries via the copper(I)-catalyzed modern version of the classical Huisgen 1,3-dipolar cycloaddition of azides to alkynes. Up to four 1,4-disubstituted 1,2,3-triazole rings bearing carbon-linked glycosyl fragments were constructed on various scaffolds via multiple cycloadditions of suitably polyfunctionalized calix[4]arene, adamantane

  通过铜（I）催化的叠氮化物与炔烃的经典Huisgen 1,3-偶极环加成反应的现代版本，已经为制备三唑糖簇库铺平了道路。通过适当多官能化的杯[4]芳烃，金刚烷和苯衍生物与乙炔基和叠氮甲基C-的多次环加成，在各种支架上最多构建四个带有碳连接糖基片段的1,4-二取代的1,2,3-三唑环。糖苷。每次环加成反应都具有很高的区域选择性，从而以非常高的收率只产生1，4-二取代的三唑环，其平均收率高达98％。这种方法的高效率及其广泛的范围构成了将各种糖单元连接到多官能化底物上的简单实用方法。
• Substituierte Aminosäurederivate
  申请人：BAYER AG

  公开号：EP0832898A2

  公开（公告）日：1998-04-01

  Die Erfindung betrifft mit Kohlenhydraten substituierte Aminosäuren der Formel worin die Substituenten die in der Beschreibung angegebene Bedeutung haben, ihre Herstellung durch Mehrkomponentenreaktion und ihre Verwendung.

  本发明涉及式如下的碳水化合物取代氨基酸 式中取代基的含义、通过多组分反应制备这些氨基酸及其用途。
• Addressing the scope of the azide–nitrile cycloaddition in glycoconjugate chemistry. The assembly of C-glycoclusters on a calix[4]arene scaffold through tetrazole spacers
  作者：Alessandro Dondoni、Alberto Marra

  DOI：10.1016/j.tet.2007.03.045

  日期：2007.7

  New glycoclusters constituted of ribosylmethyl, galactosylmethyl, and glucosylmethyl fragments assembled on a calix[ 4] arene platform by means of propoxytetrazole spacers have been prepared by coupling the corresponding sugar azides with p-toluenesulfonyl cyanide, and then reacting 1-glycosylmethyl-5-sulfonyl-tetrazole derivatives thus formed with a calix[ 4] arene tetrol. (c) 2007 Elsevier Ltd. All rights reserved.