Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside | 68622-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6S)-5-azido-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 68622-25-3
• 化学式: C₂₈H₃₁N₃O₅
• 分子量: 489.571
• InChiKey: VVOBVFJZRFWDQI-DFLSAPQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以100%的产率得到methyl 2,3,6-tri-O-benzyl-4-amino-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  pseudo假二糖

  摘要：

  描述了几种基于氨基吡喃葡萄糖的am假二糖的合成。由于与糖酵解中涉及的还原和非还原吡喃糖单元的结构相似，它们可以用作糖苷酶抑制剂。

  DOI：

  10.1016/0040-4039(93)88054-m
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以99%的产率得到Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  pseudo假二糖

  摘要：

  描述了几种基于氨基吡喃葡萄糖的am假二糖的合成。由于与糖酵解中涉及的还原和非还原吡喃糖单元的结构相似，它们可以用作糖苷酶抑制剂。

  DOI：

  10.1016/0040-4039(93)88054-m

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 glucose derivatives modified at the 4-OH as potential chain-terminators of cellulose biosynthesis; herbicidal activity of simple monosaccharide derivatives
  作者：Emma van Dijkum、Ramona Danac、David J. Hughes、Richard Wood、Anne Rees、Brendan L. Wilkinson、Antony J. Fairbanks

  DOI：10.1039/b820830a

  日期：——

  A series of D-glucose derivatives that have been modified at C-4 were synthesised from D-galactose as potential chain terminators of cellulose biosynthesis. Two compounds displayed herbicidal activity in pre-emergence tests and in addition a cell expansion assay at higher concentrations revealed symptomology of a third compound that was indicative of inhibition of cellulose biosynthesis.

  从C-4合成了一系列在C-4修饰的D-葡萄糖衍生物D-半乳糖作为纤维素生物合成的潜在链终止剂。两种化合物在出苗前测试中显示出除草活性，此外，较高浓度的细胞扩增试验还显示出第三种化合物的症状，这表明抑制了纤维素的生物合成。
• Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors
  作者：Yoshiyuki Kobayashi、Masao Shiozaki、Osamu Ando

  DOI：10.1021/jo00113a041

  日期：1995.4

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.
• 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.