tert-butyl {[1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl]methyl}carbamate | 1236065-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl {[1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl]methyl}carbamate
• 英文别名: tert-butyl N-[[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methyl]carbamate
• CAS: 1236065-90-9
• 化学式: C₁₄H₂₄N₄O₇
• 分子量: 360.367
• InChiKey: LXWGDVGZEUOPAY-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  159
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl {[1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl]methyl}carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(2R,3R,4S,5S,6R)-2-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  通过CuAAC“点击化学”合成α-和β-D-吡喃葡萄糖基三唑：反应物耐受性、反应速率、产物结构和葡萄糖苷酶抑制特性。

  摘要：

  Cu(I) 催化的叠氮化物炔烃 1,3-偶极环加成 (CuAAC)“点击化学”用于组装 21 种 α-D-和β-D-吡喃葡萄糖基三唑的库，它们被评估为潜在的糖苷酶抑制剂。在这项工作的过程中，注意到了在 CuAAC 条件下异构 α-和β-吡喃葡萄糖基叠氮化物的不同反应性。使用竞争反应进一步研究了这种差异，并在 X 射线晶体学数据的基础上进行了合理化，这揭示了 α-和 β-端基异构体的叠氮基团内键长的显着差异。结构研究还表明，在固态α-和β-葡糖基三唑中，糖和三唑环倾向于垂直取向。测定了三唑库对甜杏仁β-葡萄糖苷酶(GH1) 和酵母α-葡萄糖苷酶(GH13) 的抑制作用，从而确定了一组在100 microM 范围内有效的葡萄糖苷酶抑制剂。正如预期的那样，对一种酶的抑制优先于另一种酶被证明取决于抑制剂的异头构型。

  DOI：

  10.1016/j.carres.2010.03.041
• 作为产物：
  描述：

  N-Boc-氨基丙炔 在 copper(l) iodide 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 tert-butyl {[1-(β-D-glucopyranosyl)-1,2,3-triazol-4-yl]methyl}carbamate
  参考文献：
  名称：

  Synthesis of 4-amidomethyl-1-glucosyl-1,2,3-triazoles and evaluation as glycogen phosphorylase inhibitors

  摘要：

  Glycogen phosphorylase (GP) appears as a key enzyme for the control of hyperglycemia in the context of type 2 diabetes. In order to gain additional data for structure-activity studies of the inhibition of this enzyme, a series of eight GP inhibitor candidates were prepared from peracetylglucopyranosyl azide 1 by click-chemistry. The need for a N-Boc-protected propargylamine was identified in the CuAAC with azide 1 under Meldal's conditions, while Sharpless' conditions were better adapted to the CuAAC of azide 1 with propargyl bromide. Cycloaddition of Boc-propargylamine with azide 1 afforded the N-Boc precursor of a 4-aminomethyl-1-glucosyl-1,2,3-triazole which gave access to a series of eight amide and sulfonamide derivatives. After deacetylation, enzymatic studies revealed poor to moderate inhibitions toward this enzyme. The N-Boc-protected amine was the best inhibitor (IC50 = 620 mu M) unexpectedly slightly better than the 2-naphthylamido substituted analogue (IC50 = 650 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.10.009

文献信息

• Gram scale production of 1-azido-β-<scp>d</scp>-glucose <i>via</i> enzyme catalysis for the synthesis of 1,2,3-triazole-glucosides
  作者：Jaggaiah N. Gorantla、Salila Pengthaisong、Sunaree Choknud、Teadkait Kaewpuang、Tanaporn Manyum、Vinich Promarak、James R. Ketudat Cairns

  DOI：10.1039/c9ra00736a

  日期：——

  The production of analytical amounts of azido sugars is used as a means of verifying catalytic acid/base mutations of retaining glycosidase, but application of this process to preparative synthesis has not been reported. The catalytic acid/base mutant of Thermoanaerobacterium xylanolyticus GH116 β-glucosidase, TxGH116D593A, catalyzed the gram scale production of 1-azido-β-D-glucose (1) from p-nitr

  分析量的叠氮基糖的产生被用作验证保留糖苷酶的催化酸/碱突变的一种手段，但该方法在制备合成中的应用尚未见报道。Thermoanaerobacterium xylanolyticus GH116 β-葡萄糖苷酶的催化酸/碱突变体Tx GH116D593A 催化从对硝基苯基-β-D-吡喃葡萄糖苷 ( p NPGlc )和通过转葡萄糖基化反应叠氮化物。酶与p NPGlc 和 NaN 3在水性 MES 缓冲液 (pH 5.5) 中在 55 °C 下过夜反应产生1 (3.27 g)，其被分离为白色泡沫状固体，产率为 96%。该1已成功用于通过点击化学合成十五种含有多种官能团的1,2,3-三唑-β- D-葡萄糖基衍生物 ( 2-16 )。
• Synthesis of α- and β-d-glucopyranosyl triazoles by CuAAC ‘click chemistry’: reactant tolerance, reaction rate, product structure and glucosidase inhibitory properties
  作者：Simone Dedola、David L. Hughes、Sergey A. Nepogodiev、Martin Rejzek、Robert A. Field

  DOI：10.1016/j.carres.2010.03.041

  日期：2010.6

  cycloaddition (CuAAC) 'click chemistry' was used to assemble a library of 21 alpha-D- and beta-D-glucopyranosyl triazoles, which were assessed as potential glycosidase inhibitors. In the course of this work, different reactivities of isomeric alpha- and beta-glucopyranosyl azides under CuAAC conditions were noted. This difference was further investigated using competition reactions and rationalised on the

  Cu(I) 催化的叠氮化物炔烃 1,3-偶极环加成 (CuAAC)“点击化学”用于组装 21 种 α-D-和β-D-吡喃葡萄糖基三唑的库，它们被评估为潜在的糖苷酶抑制剂。在这项工作的过程中，注意到了在 CuAAC 条件下异构 α-和β-吡喃葡萄糖基叠氮化物的不同反应性。使用竞争反应进一步研究了这种差异，并在 X 射线晶体学数据的基础上进行了合理化，这揭示了 α-和 β-端基异构体的叠氮基团内键长的显着差异。结构研究还表明，在固态α-和β-葡糖基三唑中，糖和三唑环倾向于垂直取向。测定了三唑库对甜杏仁β-葡萄糖苷酶(GH1) 和酵母α-葡萄糖苷酶(GH13) 的抑制作用，从而确定了一组在100 microM 范围内有效的葡萄糖苷酶抑制剂。正如预期的那样，对一种酶的抑制优先于另一种酶被证明取决于抑制剂的异头构型。
• Synthesis of 4-amidomethyl-1-glucosyl-1,2,3-triazoles and evaluation as glycogen phosphorylase inhibitors
  作者：David Goyard、Tibor Docsa、Pál Gergely、Jean-Pierre Praly、Sébastien Vidal

  DOI：10.1016/j.carres.2014.10.009

  日期：2015.1

  Glycogen phosphorylase (GP) appears as a key enzyme for the control of hyperglycemia in the context of type 2 diabetes. In order to gain additional data for structure-activity studies of the inhibition of this enzyme, a series of eight GP inhibitor candidates were prepared from peracetylglucopyranosyl azide 1 by click-chemistry. The need for a N-Boc-protected propargylamine was identified in the CuAAC with azide 1 under Meldal's conditions, while Sharpless' conditions were better adapted to the CuAAC of azide 1 with propargyl bromide. Cycloaddition of Boc-propargylamine with azide 1 afforded the N-Boc precursor of a 4-aminomethyl-1-glucosyl-1,2,3-triazole which gave access to a series of eight amide and sulfonamide derivatives. After deacetylation, enzymatic studies revealed poor to moderate inhibitions toward this enzyme. The N-Boc-protected amine was the best inhibitor (IC50 = 620 mu M) unexpectedly slightly better than the 2-naphthylamido substituted analogue (IC50 = 650 mu M). (C) 2014 Elsevier Ltd. All rights reserved.