methyl 2-azido-2-deoxy-D-glucopyranoside | 273749-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-2-deoxy-D-glucopyranoside
• 英文别名: methyl 2-azido-2-deoxy-α/β-D-glucopyranoside；(2R,3S,4R,5R)-5-azido-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• CAS: 273749-59-0
• 化学式: C₇H₁₃N₃O₅
• 分子量: 219.197
• InChiKey: QYZPIZZUWJKSTF-YDEIVXIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127.91
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-deoxy-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 生成 Methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  抗凝血五糖磺达肝素的全合成

  摘要：

  抗凝五糖磺达肝素是使用改进和优化的合成策略合成的，包括收敛的[3 + 2]偶联方法，正交保护基和各种糖基供体。糖基化的新方法也用于控制立体化学构型和提高糖基化的产率。另外，采用HPLC和NMR方法监测磺达肝素的全合成过程。这项工作在相关文献的基础上为磺达肝素的合成和分析提供了详尽的阐述，并为肝素样低聚糖的合成提供了丰富的信息。

  DOI：

  10.1002/cmdc.201400019
• 作为产物：
  描述：

  2-deoxy-2-amino glucose 在 盐酸 、 triflic azide 、 copper(II) sulfate 、 三乙胺 作用下， 以 水 为溶剂， 生成 methyl 2-azido-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU

  摘要：

  GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D-glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-alpha-D-glucopyranoside 6-phosphate (1 alpha), methyl 2-amino-2deoxyl-beta-D-glucopyranoside 6-phosphate (1 beta), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-alpha-D-glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-alpha-Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1 alpha, 1 beta, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1 beta, 1 beta and 2 were inactive against GlmM and GlmU even at high concentrations. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.024

文献信息

• Ferrier Carbocyclization-Mediated Synthesis of Enantiopure Azido Inositol Analogues
  作者：Alex P. Ausmus、Maxwell Hogue、Justin L. Snyder、Sarah R. Rundell、Krestina M. Bednarz、Nicholas Banahene、Benjamin M. Swarts

  DOI：10.1021/acs.joc.9b03064

  日期：2020.3.6

  InoAz analogues starting from readily available azido glucosides. Using this approach combined with a para-methoxybenzyl protecting group strategy, 3-azido-3-deoxy- and 4-azido-4-deoxy-d-myo-inositol were efficiently synthesized. 5-Azido-5-deoxy-d-myo-inositol was inaccessible due to an unusual β-elimination reaction, wherein the azide anion acted as the leaving group. The reported strategy is expected

  叠氮化物修饰的肌醇（InoAz）类似物作为抑制剂很有价值，并有望作为代谢化学报告分子（MCR）用于标记真核细胞和分枝杆菌中含肌醇的糖结合物，但是通过传统方法合成对映体纯的InoAz类似物具有挑战性。作为一种补充途径，在这里我们研究了Ferrier碳环化反应在从容易获得的叠氮基糖苷开始的对映纯InoAz类似物合成中的应用。使用此方法与对甲氧基苄基保护基策略相结合，有效地合成了3-azido-3-deoxy-和4-azido-4-deoxy-d-myo-inositol。由于不寻常的β-消除反应，其中叠氮化物阴离子充当离去基团，因此无法获得5-叠氮基5-脱氧-d-肌醇。
• Fluorous-Assisted Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides
  作者：Chao Cai、Demetria M. Dickinson、Lingyun Li、Sayaka Masuko、Matt Suflita、Victor Schultz、Shawn D. Nelson、Ujjwal Bhaskar、Jian Liu、Robert J. Linhardt

  DOI：10.1021/ol500738g

  日期：2014.4.18

  The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag. attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate. oligosaccharides were successfully synthesized employing fluorous techniques.
• Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors
  作者：Ying Zhou、Feng Lin、Jianfang Chen、Biao Yu

  DOI：10.1016/j.carres.2006.02.020

  日期：2006.7

  Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of a tetrasaccharide substrate of heparanase
  作者：Jianfang Chen、Ying Zhou、Chen Chen、Weichang Xu、Biao Yu

  DOI：10.1016/j.carres.2008.06.011

  日期：2008.11

  A tetrasaccharide, corresponding to the heparan sulfate heparanase substrate, namely beta-D-GIcA(2S)-(1 -> 4)-alpha-D-GIcN(NS,6S)-(1 -> 4)-beta-D-GIcA-(1 -> 4)-alpha-D-GIcN(NS,6S)-OMe, was synthesized in a convergent manner via coupling of a pair of the disaccharide building blocks as a key step. (C) 2008 Elsevier Ltd. All rights reserved.