2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl azide | 150370-49-3

• 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-benzyl-β-D-mannopyranosyl azide
• 英文别名: 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylazide；(2R,3S,4S,5R,6R)-2-azido-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 150370-49-3
• 化学式: C₃₄H₃₅N₃O₅
• 分子量: 565.669
• InChiKey: NKVQKPBQIGZTBQ-ZYSDIQSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl azide 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 2.5h， 生成 2-chloro-N-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)benzamide
  参考文献：
  名称：

  Rao, C. Srinivas; Ratcliffe, Andrew J.; Fraser-Reid, Bert, Journal of the Chemical Society. Perkin transactions I, 1993, # 11, p. 1207 - 1212

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(乙酰氧基甲基)-6-叠氮基四氢-2H-吡喃-3,4,5-三基三乙酸酯 在 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl azide
  参考文献：
  名称：

  Rao, C. Srinivas; Ratcliffe, Andrew J.; Fraser-Reid, Bert, Journal of the Chemical Society. Perkin transactions I, 1993, # 11, p. 1207 - 1212

  摘要：

  DOI：

文献信息

• Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate
  作者：Masanori Mizuno、Takayuki Shioiri、Masanori Mizuno

  DOI：10.1039/a705768g

  日期：——

  The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.

  使用双（对硝基苯基）磷酸酰肼和DBU，可以高效地将各种醇和己糖吡喃转化为相应的烷基叠氮化物和糖苷叠氮化物。
• Total Synthesis of Spicamycin
  作者：Tamotsu Suzuki、Sayaka T. Suzuki、Iwao Yamada、Yoshiaki Koashi、Kazue Yamada、Noritaka Chida

  DOI：10.1021/jo010925c

  日期：2002.5.1

  The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-beta-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization

  描述了一种角霉素同系物SPM VIII（3）的第一个全合成。初步模型研究使用四-O-苄基-β-D-甘露吡喃糖胺（13）和卤尿嘧啶5构建穗霉素中的特征性N-糖苷键，结果表明，钯催化条件成功提供了良好收率的偶联产物14和15 。还显示出N-糖苷的热异构化容易发生，这导致主要形成β-端基异构体作为热力学上有利的化合物，并且估计15的端基异构化的活化能约为1。30大卡/摩尔 斯皮霉素6的新型氨基庚糖单元是通过无环醛的碳延伸立体选择性地制备的，通过衍生自天然丰富的肌醇的高度官能化的环己烷的裂解反应制备。β-庚基吡喃糖胺6与受保护的6-氯嘌呤5d的Pd催化偶联反应，然后脱保护，提供了角霉素氨基核苷2，其与十二烷酰基甘氨酸的缩合完成了3的全合成。这项研究证实了新型化合物的拟议独特结构核苷抗生素。
• Stereoselective synthesis of glycosyl azides from anomeric hydroxides via protecting group manipulations
  作者：Sourav Nayak、Somnath Yadav

  DOI：10.1016/j.carres.2023.108739

  日期：2023.1

  report the direct conversion of anomeric hydroxides to glycosyl azides in one step using diphenylphosphoryl azide. Protecting group manipulations on the hexose sugars have enabled the stereoselective synthesis of either the α-glycosyl azides or the β-anomeric azides in moderate to very good yields. The reaction has also been successfully used to enable the synthesis of β-2-deoxy-2-aminoglucosyl azides

  在此，我们报告了使用二苯基磷酰叠氮化物一步将端基氢氧化物直接转化为糖基叠氮化物。己糖上的保护基团操作使得能够以中等到非常好的收率立体选择性合成 α-糖基叠氮化物或 β-异头叠氮化物。该反应也已成功用于合成 β-2-脱氧-2-氨基葡萄糖基叠氮化物。
• Synthesis of novel N-glycoside derivatives via CuSCN-catalyzed reactions and their SGLT2 inhibition activities
  作者：Shao-Tao Bai、De-Cai Xiong、Youhong Niu、Yan-Fen Wu、Xin-Shan Ye

  DOI：10.1016/j.tet.2015.05.108

  日期：2015.7

  A convenient approach to the synthesis of novel triazole-N-glycoside derivatives was developed via CuSCN-catalyzed click reaction and Ullmann-type coupling reaction for the first time. The SGLT2 inhibitory activities of these synthetic N-glycosides were evaluated, and some compounds showed moderate SGLT2 inhibition activities at 100 nM. The results could benefit the discovery of new SGLT2 inhibitors for the treatment of diabetes. (C) 2015 Elsevier Ltd. All rights reserved.
• “Click” Saccharide/β-Lactam Hybrids for Lectin Inhibition
  作者：Claudio Palomo、Jesus M. Aizpurua、Eva Balentová、Itxaso Azcune、J. Ignacio Santos、Jesús Jiménez-Barbero、Javier Cañada、José Ignacio Miranda

  DOI：10.1021/ol8006259

  日期：2008.6.5

  Hybrid glycopeptide beta-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "click" cycloaddition reaction, and as shown by NMR/MD experiments, binding of the resulting mimetics to Ulex Europaeus Lectin-1 (UEL-1) occurred after a "bent-to-extended" conformational change around a partially rotatable triazolylmethylene moiety.