ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside | 166516-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-azido-6-ethylsulfanyl-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 166516-68-3
• 化学式: C₈H₁₅N₃O₄S
• 分子量: 249.291
• InChiKey: AYRZSNUFRWMSGE-PVFLNQBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 在 palladium on activated charcoal 、 (bis(diphenylphosphino)ethylene)(1,5-cyclooctadiene)iridium(I) hexafluorophosphate 四氮唑 、 盐酸 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 二氯二茂锆 、 4 A molecular sieve 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 水 、 氢气 、 silver trifluoromethanesulfonate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、689.48 kPa 条件下， 反应 83.42h， 生成 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
  参考文献：
  名称：

  提议的胰岛素第二信使糖基肌醇磷酸酯的一部分和糖基磷脂酰肌醇锚固体的内芯的合成

  摘要：

  合成6- ø - （2-氨基-2-脱氧- α-d-D-吡喃葡萄糖基）-D-肌醇-1-磷酸，内芯结构中的各种glycosylphosphatidylinositols找到，并且相应的1,2-环磷酸酯，描述了作为胰岛素第二信使糖基肌醇磷酸酯的一部分提出的方法。分子的肌醇部分中的手性是通过使用已知的D-樟脑缩醛中间体来实现的。糖基化使用4 - O-烯丙基-2-叠氮基3，6-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖基氟作为糖基供体。烯丙基可以被化学选择性地去除，从而打开了一条与葡糖胺单元的4位结合的寡糖的途径。磷酸化通过氨基磷酸酯方法完成。

  DOI：

  10.1016/s0040-4020(97)10238-1
• 作为产物：
  描述：

  ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 triflic azide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到ethyl 2-azido-2-deoxy-1-thio-β-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

• Facile preparation of glycosyl donors for oligosaccharide synthesis: 2-azido-2-deoxyhexopyranosyl building blocks
  作者：Therese Buskas、Per J. Garegg、Peter Konradsson、Jean-Luc Maloisel

  DOI：10.1016/s0957-4166(00)86294-1

  日期：1994.11

  Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described. These are useful intermediates for the synthesis of oligo-saccharides containing alpha-D-2-amino-2-deoxy (or 2-acetamido-2-deoxy) hexosyl residues in the galacto-, gluco-, and manno- series.
• Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of <i>Moraxella catarrhalis</i>
  作者：Kerstin Ekelöf、Stefan Oscarson

  DOI：10.1021/jo960789p

  日期：1996.1.1

  The synthesis of the octasaccharide [p-(trifluoroacetamido)phenyl]ethyl 4-O-[2-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]-6-O-[2-O-[4-O-(4-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-O-beta-D-glucopyranosyl-alpha-D-glucopyranoside, representing the outer part of the lipooligosaccharide from Moraxella catarrhalis serotype A, is described, together with a hepta-, a hexa-, and a pentasaccaride, composing parts thereof with shorter oligosaccharide chains substituted in the g-position of the central 3,4,6-branched glucose moiety. The versatility of the use of thioglycosides in oligosaccharide synthesis is shown, since throughout the synthesis thioglycosides are used as glycosyl donor precursors, either directly in dimethyl(methylthio)sulfonium triflate (DMTST)-promoted coupling reactions or after conversion to the corresponding glycosyl bromide in silver triflate-promoted couplings. The effects of different protecting groups, anomeric leaving groups, and solvents used in the various coupling reactions are often substantial, which necessitates the use of easily convertible intermediates.
• Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU
  作者：Yongmeng Li、Yan Zhou、Yufang Ma、Xuebing Li

  DOI：10.1016/j.carres.2011.05.024

  日期：2011.9

  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.
• Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors
  作者：Per J. Garegg、Peter Konradsson、Stefan Oscarson、Katinka Ruda

  DOI：10.1016/s0040-4020(97)10238-1

  日期：1997.12

  2-cyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor acetal intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride as glycosyl donor. The allyl group can be chemoselectively removed, opening a route to oligosaccharides

  合成6- ø - （2-氨基-2-脱氧- α-d-D-吡喃葡萄糖基）-D-肌醇-1-磷酸，内芯结构中的各种glycosylphosphatidylinositols找到，并且相应的1,2-环磷酸酯，描述了作为胰岛素第二信使糖基肌醇磷酸酯的一部分提出的方法。分子的肌醇部分中的手性是通过使用已知的D-樟脑缩醛中间体来实现的。糖基化使用4 - O-烯丙基-2-叠氮基3，6-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖基氟作为糖基供体。烯丙基可以被化学选择性地去除，从而打开了一条与葡糖胺单元的4位结合的寡糖的途径。磷酸化通过氨基磷酸酯方法完成。