1-N-(1-benzyl N-(tert-butyloxycarbonyl)-4-aspart-4-oyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine | 78028-93-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 1-N-(1-benzyl N-(tert-butyloxycarbonyl)-4-aspart-4-oyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
• 英文别名: benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]butanoate
• CAS: 78028-93-0
• 化学式: C₃₀H₄₀N₂O₁₄
• 分子量: 652.653
• InChiKey: JVQHRGLBHICPLH-KCJQSDGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  208
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-N-(1-benzyl N-(tert-butyloxycarbonyl)-4-aspart-4-oyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2,3,4,6-tetra-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl]-D-glucopyranosylamine
  参考文献：
  名称：

  含有葡萄糖-天冬酰胺键的高甘露糖型糖肽类似物的合成。

  摘要：

  通过将寡糖酶促转移至含有Glc-Asn键的合成五肽中来制备标题化合物。该化合物没有被植物和细菌来源的糖酰胺酶水解，但在微摩尔范围内抑制了这两种酶。将其活性与其他潜在抑制剂进行了比较。

  DOI：

  10.1016/s0960-894x(98)00306-0
• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 platinum(IV) oxide 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-N-(1-benzyl N-(tert-butyloxycarbonyl)-4-aspart-4-oyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
  参考文献：
  名称：

  含有葡萄糖-天冬酰胺键的高甘露糖型糖肽类似物的合成。

  摘要：

  通过将寡糖酶促转移至含有Glc-Asn键的合成五肽中来制备标题化合物。该化合物没有被植物和细菌来源的糖酰胺酶水解，但在微摩尔范围内抑制了这两种酶。将其活性与其他潜在抑制剂进行了比较。

  DOI：

  10.1016/s0960-894x(98)00306-0

文献信息

• Stereoselective N-Glycosylation by Staudinger Ligation
  作者：Yi He、Ronald J. Hinklin、Jiyoung Chang、Laura L. Kiessling

  DOI：10.1021/ol048271s

  日期：2004.11.1

  Stereoselective methods for the chemical synthesis of beta-N-glycosyl amides are needed to generate glycopeptides and glycoproteins. Here, we report that the Staudinger ligation can be used to form glycosylated asparagine derivatives. The reaction proceeds with high stereoselectivity, and a variety of glycosyl azides can function as substrates. Our results provide precedence for the use of this powerful

  需要化学合成β-N-糖基酰胺的立体选择方法来产生糖肽和糖蛋白。在这里，我们报告Staudinger连接可以用来形成糖基化的天冬酰胺衍生物。该反应以高的立体选择性进行，并且多种糖基叠氮化物可以用作底物。我们的结果为这种强大的酰胺键形成反应用于N-糖肽合成提供了先例。[反应：看文字]
• An easy access to anomeric glycosyl amides and imines(Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides
  作者：László Kovács、Erzsébet Ősz、Valéria Domokos、Wolfgang Holzer、Zoltán Györgydeák

  DOI：10.1016/s0040-4020(01)00380-5

  日期：2001.5

  The preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied. Starting from the appropriate glycosyl azides and trialkyl or triaryl phosphines, the corresponding phosphinimides were obtained by modified Staudinger reactions. The latter compounds were readily converted into 1-N-acyl-gluco- and galactopyranosyl amines with high yields by applying activated

  研究了异头糖基次膦酰亚胺的制备及在合成中的应用。从合适的糖基叠氮化物和三烷基或三芳基膦开始，通过改良的施陶丁格反应获得相应的亚膦酰亚胺。通过使用活化的酸衍生物或简单的羧酸，后一种化合物容易以高收率转化成1 - N-酰基-葡萄糖-和吡喃半乳糖基胺。通过氮杂-维蒂希反应分别使用脂族或芳族醛，获得1- N-亚烷基-亚芳基次膦酸酯或席夫碱（席夫碱）。
• Synthesis of upper rim calix[4]arene divalent glycoclusters via amide bond conjugation
  作者：Uta Schädel、Francesco Sansone、Alessandro Casnati、Rocco Ungaro

  DOI：10.1016/j.tet.2004.11.048

  日期：2005.1

  Synthetic routes for linking two sugar units at the upper rim of cone calix[4]arenes, through the formation of amide bonds, have been explored. Steric effects prevent the coupling of calix[4]arene dicarboxylic acid with simple aminoglycosides, whereas the corresponding reaction with carbohydrates bearing a two or three carbon atoms spacer, terminating with a primary amino group, allows the synthesis of several difunctionalized calix[4]arene neoglycoconjugates, attractive in chemical glycobiology and supramolecular chemistry. (C) 2004 Elsevier Ltd. All rights reserved.
• Solid-phase synthesis of two glycopeptides containing the amino acid sequence 5 to 9 of somatostatin
  作者：Solange Lavielle、Nicolas C. Ling、Roger C. Guillemin

  DOI：10.1016/s0008-6215(00)85247-7

  日期：1981.3

  2,3,4,6-Tetra-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-D-g lucopyranosylamine and 2-acetamido-3,4,6-tri-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-2 -deoxy-D-glucopyranosylamine were introduced, respectively, by the solid-phase procedure in the amino acid sequence 5 to 9 of somatostatin. The two resulting glycopeptides beta-D-Glcp-(1 leads to 4)- and beta-D-GlcpNAc-(1 leads to 4)-Asn-Phe-Phe-Trp-Lys-OH were homogeneous on examination by t.l.c. and l.c., and their structures were confirmed by m.s. of the N-acetyl, permethyl derivatives.
• GUILLEMIN, R. C. L.;LAVIELLE, S.;BRAZEAU, P. E. ,, JR;LING, N. C.;BENOIT,+
  作者：GUILLEMIN, R. C. L.、LAVIELLE, S.、BRAZEAU, P. E. ,, JR、LING, N. C.、BENOIT,+

  DOI：——

  日期：——