(2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine | 204510-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS: 204510-88-3
• 化学式: C₂₇H₂₇N₃O₅
• 分子量: 473.528
• InChiKey: ZMQDWRVORRUOJR-MSXPJASTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 三乙基硅烷 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2,3,6-tri-O-benzyl-β-D-galactopyranosyl azide
  参考文献：
  名称：

  Reverse-CD mimics with flexible linkages offer adaptable cavity sizes for guest encapsulation

  摘要：

  我们合成了具有可调整空腔大小的反向-CD 模拟物。单晶结构测定和客体结合研究证明了这种适应性。

  DOI：

  10.1039/c3cc47734g
• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.17h， 生成 (2S,4aR,6R,7R,8S,8aS)-6-Azido-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Reverse-CD mimics with flexible linkages offer adaptable cavity sizes for guest encapsulation

  摘要：

  我们合成了具有可调整空腔大小的反向-CD 模拟物。单晶结构测定和客体结合研究证明了这种适应性。

  DOI：

  10.1039/c3cc47734g

文献信息

• A versatile solvent-free azide–alkyne click reaction catalyzed by in situ generated copper nanoparticles
  作者：Atchutarao Pathigoolla、Ramachandra P. Pola、Kana M. Sureshan

  DOI：10.1016/j.apcata.2012.12.025

  日期：2013.2

  A general, high-yielding and efficient methodology for the copper catalyzed azide–alkyne cycloaddition (CuAAC) reaction catalyzed by in situ generated copper nanoparticles (CuNPs) or their clusters is reported. This simple reaction is facile in water, organic solvents and solvent-free conditions under ambient, open-air conditions and requires no special reaction conditions and chromatographic separation

  报告了一种由原位生成的铜纳米粒子（CuNPs）或其簇催化的铜催化的叠氮化物-炔烃环加成反应（CuAAC）的通用，高产且高效的方法。这种简单的反应易于在环境，露天条件下的水，有机溶剂和无溶剂条件下进行，并且不需要特殊的反应条件和色谱分离。
• 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。
• A galabiose-based two-dimensional scaffold for the synthesis of inhibitors targeting Pk- and P-antigen binding proteins
  作者：Jörgen Ohlsson、Ulf J. Nilsson

  DOI：10.1016/s0040-4039(03)00475-1

  日期：2003.3

  A disaccharide scaffold based on galabiose (Galal-4Gal) was synthesized. Four different acceptors were evaluated in the alpha-galactosylation and a relationship between the nucleophilicity, yield, and alpha/beta-selectivity was found. The scaffold contains two orthogonal derivatisation sites, i.e. at O-2' and the anomeric position, and as proof of concept, one derivatised galabioside was synthesized. Compounds based on this galabiose-scaffold are potential inhibitors of P- and P-k-antigen binding proteins. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Reverse-CD mimics with flexible linkages offer adaptable cavity sizes for guest encapsulation
  作者：Atchutarao Pathigoolla、Kana M. Sureshan

  DOI：10.1039/c3cc47734g

  日期：——

  Reverse-CD mimics with adaptable cavity sizes have been synthesized. The adaptability has been demonstrated through single crystal structure determination and guest binding studies.

  我们合成了具有可调整空腔大小的反向-CD 模拟物。单晶结构测定和客体结合研究证明了这种适应性。