methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside | 54522-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(azidomethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 54522-58-6
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: XCNACVWQDZTZEB-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside 在 四丁基溴化铵 、 caesium carbonate 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 75.0h， 生成 bis-1,11-[methyl-6-azido-2,3-di-O-benzyl-6-deoxy-4-yloxy-α-D-glucopyranoside]-(6-tosyl-3,9-dioxa-6-aza-undecane)
  参考文献：
  名称：

  Synthesis of carbohydrate-based azamacrocycles by Richman–Atkins cyclisation

  摘要：

  摘要 对称氮含量环结构及其包含两个或四个葡萄糖单元的化合物可以容易地从可获得的单糖构建单元中获得。通过4,4'-位和6,6'-位的各种连接方式，得到了各种前体，这些前体通过Richman–Atkins环化反应，采用不同的桥接单元连续转化，最终形成了明确的糖芳烃冠醚。

  DOI：

  10.1016/j.crci.2010.03.032
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 sodium azide 、 碘 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  单击化学途径到三环单糖三唑杂化物：取代的六氢-4 H-吡喃并[2,3- f ] [1,2,3]三唑[5,1- c ] [1,4]奥氮平的设计与合成†

  摘要：

  一种单击化学方法，用于新型三环单糖三唑杂化物，即芳基取代的六氢-4 H-吡喃并[2,3- f ] [1,2,3]三唑并[5,1- c ] [1,4]奥氮平衍生物已经报道了由6-叠氮基-4 - O-炔丙基糖吡喃糖苷的分子内1，3-偶极环加成反应。

  DOI：

  10.1039/c4ra11035h

文献信息

• Intramolecular Metal-Free C(sp³)-H Activation Enables a Selective Mono <i>O</i>-Debenzylation of Fully Protected Aminosugars
  作者：Andrés G. Santana、Antonio J. Herrera、Concepción C. González

  DOI：10.1021/acs.joc.1c01977

  日期：2021.12.3

  Carbamate-bearing benzylated aminosugars undergo an I2/I(III)-promoted intramolecular hydrogen atom transfer (IHAT) followed by a nucleophilic attack to provide polycyclic structures. Thus, suitably positioned benzyl ethers are surgically oxidized into the corresponding mixed N/O-benzylidene acetals, which can be conveniently deprotected under mild acidic conditions to grant access to selectively O-deprotected

  带有氨基甲酸酯的苄基化氨基糖经历 I 2 /I(III) 促进的分子内氢原子转移 (IHAT)，然后进行亲核攻击以提供多环结构。因此，适当定位的苄基醚通过外科手术氧化成相应的混合N / O-亚苄基缩醛，可以在温和的酸性条件下方便地对其进行脱保护，从而获得选择性的O-脱保护氨基糖，以便进一步衍生化。该策略的范围已通过一系列呋喃和吡喃支架得到证实。包括 Hammett LFER 和 KIE 分析在内的初步机理研究支持以亲核环化作为速率决定步骤的反应途径。
• Synthesis of benzolactams by 11-endo selective aryl radical cyclisation of 2-iodobenzamides
  作者：Maria A. F. Prado、Ricardo J. Alves、José D. Souza Filho、Rosemeire B. Alves、Maria T. C. Pedrosa、Renata F. Prado、André A. G. Faraco

  DOI：10.1039/b002416n

  日期：——

  Regioselective 11-endo aryl radical cyclisation of methyl 4-O-allyl-2,3-di-O-benzyl-6-deoxy-6-(2-iodobenzoylamino)-α-D-glucopyranoside 4 and N-(3-allyloxypropyl)-2-iodobenzamide 9 with tri-n-butyltin hydride provided the benzolactams 5 and 10, respectively. The unequivocal structures of 5 and 10 were supported by 1H and 13C NMR spectroscopy and by PENDANT or DEPT, COSY and HMQC experiments.

  甲基4-O-烯丙基-2,3-二-O-苄基-6-脱氧-6-(2-碘苯甲酰氨基)-α-D-吡喃葡萄糖苷4与N-(3-烯丙氧基丙基)-2-碘苯甲酰胺9在三丁基锡氢化物作用下，分别通过11-内向芳基自由基环化反应，得到了苯并内酰胺5和10。5和10的确定结构得到了1H和13C核磁共振光谱、PENDANT或DEPT、COSY以及HMQC实验的支持。
• A short route for the synthesis of “sweet” macrocycles via a click-dimerization–ring-closing metathesis approach
  作者：Simon Dörner、Bernhard Westermann

  DOI：10.1039/b502682b

  日期：——

  A facile and flexible approach for the preparation of macrocyclic molecules containing different carbohydrate moieties is presented, employing the reaction cascade: click-dimerization and ring-closing metathesis.

  本文介绍了一种简便灵活的方法，利用级联反应：单击二聚化和闭环偏析，制备含有不同碳水化合物分子的大环分子。
• Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin
  作者：Bryan Elchert、Jie Li、Jinhua Wang、Yu Hui、Ravi Rai、Roger Ptak、Priscilla Ward、Jon Y. Takemoto、Mekki Bensaci、Cheng-Wei Tom Chang

  DOI：10.1021/jo035290r

  日期：2004.3.1

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.
• Studies of the stereoselective reduction of ketosugar (hexosulose)
  作者：Cheng-Wei Tom Chang、Yu Hui、Bryan Elchert

  DOI：10.1016/s0040-4039(01)01472-1

  日期：2001.10

  The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported, Combining Our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars, These findings are valuable in the synthesis of various carbohydrate derivatives. (C) 2001 Published by Elsevier Science Ltd.