(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)methyl amine | 113084-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)methyl amine
• 英文别名: [(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methanamine
• CAS: 113084-97-2
• 化学式: C₃₅H₃₉NO₅
• 分子量: 553.698
• InChiKey: BMSCNMNZBFNHHB-IVFJIKSYSA-N

物化性质

• 沸点：
  673.9±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)methyl amine 在 三乙烯二胺 、 (Cl₃CO)2CO 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-[Acetyl-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-amino]-2-phenyl-N-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-acetamide
  参考文献：
  名称：

  An Access to Glycoconjugate Libraries through Multicomponent Reactions

  摘要：

  Four-component reactions: The Ugi reaction of four suitably functionalized carbohydrate derivatives (as a per-O-benzylated amine, an aldehyde, a carboxylic acid, and an isocyanide) allow the effective assembly of diverse compound libraries. The complex glycoconjugates formed can be deprotected (see the picture for an example), and the resulting glycomimetics are of high interest for screening purposes.

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3436::aid-anie3436>3.0.co;2-z
• 作为产物：
  描述：

  1-(O-p-toluenesulfonyl)-3,4,5,7-tetra-O-benzyl-2,6-anhydroglucoheptitol 在 sodium tetrahydroborate 、 sodium azide 、 nickel dichloride 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)methyl amine
  参考文献：
  名称：

  An Access to Glycoconjugate Libraries through Multicomponent Reactions

  摘要：

  Four-component reactions: The Ugi reaction of four suitably functionalized carbohydrate derivatives (as a per-O-benzylated amine, an aldehyde, a carboxylic acid, and an isocyanide) allow the effective assembly of diverse compound libraries. The complex glycoconjugates formed can be deprotected (see the picture for an example), and the resulting glycomimetics are of high interest for screening purposes.

  DOI：

  10.1002/(sici)1521-3773(19981231)37:24<3436::aid-anie3436>3.0.co;2-z

文献信息

• Synthesis of thiourea-tethered C-glycosyl amino acids via isothiocyanate–amine coupling
  作者：Reham F. Barghash、Alessandro Massi、Alessandro Dondoni

  DOI：10.1039/b908156a

  日期：——

  A new class of C-glycosyl amino acids displaying a thiourea segment as a linker has been designed and synthesized by addition of peracetylated glycosylmethyl isothiocyanates to an amine-functionalized amino acid (Nα-Fmoc-β-amino-L-alanine). Three pairs of compounds with α- and β-galacto, α- and β-gluco, and α- and β-manno configuration have been prepared with yields ranging between 70 and 75%. The orthogonal set of protective groups (O-acetyl in the carbohydrate moiety and N-Fmoc in the amino acid residue) makes these compounds suitable substrates for the co-translational modification of natural peptides. The couplings of model hydroxy-free and perbenzylated glycosylmethyl isothiocyanates with the above Nα-Fmoc-β-amino-L-alanine and the Nα-Boc-protected analogue have been carried out as well, thus broadening the scope of the coupling reaction. Nevertheless, there are limitations of this isothiocyanate–amine coupling in complex systems, and these are briefly discussed.

  通过将乙酰化的糖基甲基异硫氰酸酯添加到胺功能化的氨基酸（Nα-Fmoc-β-氨基-L-丙氨酸）上，设计并合成了一类新的具有硫脲键段的C-糖基氨基酸。制备了三种分别具有α-和β-半乳糖、α-和β-葡萄糖以及α-和β-甘露糖构型的化合物，产率在70%至75%之间。保护基团（糖部分中的O-乙酰基和氨基酸残基中的N-Fmoc）的正交性使得这些化合物适合作为天然肽共翻译修饰的底物。还进行了模型无羟基和苯甲酰化的糖基甲基异硫氰酸酯与上述Nα-Fmoc-β-氨基-L-丙氨酸及其Nα-Boc保护类似物的偶联反应，从而扩大了偶联反应的范围。然而，这种异硫氰酸酯-胺偶联在复杂系统中存在局限性，这些局限性在此简要讨论。
• Substituierte Aminosäurederivate
  申请人：BAYER AG

  公开号：EP0832898A2

  公开（公告）日：1998-04-01

  Die Erfindung betrifft mit Kohlenhydraten substituierte Aminosäuren der Formel worin die Substituenten die in der Beschreibung angegebene Bedeutung haben, ihre Herstellung durch Mehrkomponentenreaktion und ihre Verwendung.

  本发明涉及式如下的碳水化合物取代氨基酸 式中取代基的含义、通过多组分反应制备这些氨基酸及其用途。