Methyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside | 242142-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3R,4R,5S,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-amine
• CAS: 242142-78-5
• 化学式: C₂₈H₃₃NO₅
• 分子量: 463.574
• InChiKey: RDCKDAKALUCYOW-FXGKLIOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  Methyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside 在 钯 环己烯 作用下， 以 乙醇 、 苯 为溶剂， 反应 38.0h， 生成 Methyl 2-deoxy-2-(2',4',6'-trihydroxyphenylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a novel pseudodisaccharide glycoside as a potential glycosidase inhibitor

  摘要：

  合成了一种N-连接伪二糖2，其中应用了肌醇基团替代了葡萄糖吡喃糖残基，以模拟在糖蛋白加工过程中被葡萄糖苷酶II水解的二糖单元3-O-(α-D-葡萄糖吡喃糖基)-D-葡萄糖吡喃糖；试图合成类似的N-连接化合物1作为葡萄糖苷酶I的抑制剂，导致了新颖的N-苯基衍生物10的形成，该衍生物来源于2-氨基-2-脱氧-D-葡萄糖吡喃糖。

  DOI：

  10.1039/a800279g
• 作为产物：
  描述：

  methyl-2-azido-3,4,5-tri-O-benzyl-2-desoxy-α-D-glucopyranoside 在 硫化氢 作用下， 以 吡啶 、 水 为溶剂， 反应 7.0h， 生成 Methyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  α-葡萄糖苷酶抑制剂的合成：曲二糖型假二糖和相关的假三糖11假糖，第38部分：第37部分，请参见参考文献[1]。

  摘要：

  摘要设计并合成了两种曲霉二糖型假二糖和一种三糖，它们含有5-氨基-1,2,3,4-环戊netetrol衍生物或缬氨酸胺，它们通过氮桥与糖残基连接，并作为加工α合成。 -葡糖苷酶I抑制剂。假二糖的合成分别从糖异硫氰酸酯和氨基环糖醇的偶联产物开始，通过用氧化汞（II）环化成环状异脲并随后脱保护来进行。通过保护的瓦伦胺和糖环氧化物的反应，然后脱保护，制备伪假二糖的收率很低。尽管拟低聚糖都是α-葡萄糖苷酶（面包酵母）的强抑制剂，

  DOI：

  10.1016/s0008-6215(98)00045-7

文献信息

• Synthesis and Characterization of Monosaccharide Derivatives and Application of Sugar-Based Prolinamides in Asymmetric Synthesis
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1002/ejoc.201200522

  日期：2012.11

  were converted into the corresponding prolinamide organocatalysts (i.e., 1a, 2a, 3a, and 3b) in high yields. The catalytic activity of these sugar-based prolinamide organocatalysts was demonstrated in asymmetric aldol reactions in various solvents and at different temperatures. The oraganocatalyst 3a was shown to be an efficient and powerful organocatalyst for the enantioselective aldol reaction of various

  首次合成、分离和使用N-乙酰氨基葡萄糖衍生物甲基2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷(9b)的β-异头体用于合成糖基伯胺4b。糖基伯胺 5a、一对单糖衍生物 6a 和 6b 以及所有这些化合物的前体也被合成、分离并通过标准光谱方法进行了充分研究，包括 1H-1H COZY 和 HSQC 等 2D NMR 光谱实验. 然后将糖基伯胺 4a、5a、6a 和 6b 以高产率转化为相应的脯氨酰胺有机催化剂（即 1a、2a、3a 和 3b）。这些糖基脯氨酰胺有机催化剂的催化活性在各种溶剂和不同温度下的不对称羟醛反应中得到证明。
• N-Linked carba-disaccharides as potential inhibitors of glucosidases I and II
  作者：Ivone Carvalho、Alan H. Haines

  DOI：10.1039/a902826i

  日期：——

  An N-linked pseudodisaccharide 2 containing an inositol moiety in place of a glycopyranosyl residue has been synthesised to mimic the disaccharide unit, 3-O-(α-D-glucopyranosyl)-D-glucopyranose, cleaved by glucosidase II during glycoprotein processing. Its inhibitory action towards yeast α-glucosidase was inferior to that of 1-deoxynojirmycin, a known inhibitor of glucosidase II. An attempt to prepare the analogous 2-N-linked compound 1 as an inhibitor of glucosidase I led to the novel N-phenyl derivative 11 of 2-amino-2-deoxy-D-glucopyranose.

  一种含有肌醇部分代替糖苷残基的N-连接假二糖2已被合成，以模拟在糖蛋白加工过程中由糖基二酯酶II切割的二糖单元3-O-(α-D-葡萄糖苷基)-D-葡萄糖苷。2对酵母α-糖苷酶的抑制作用不如已知的糖基二酯酶II抑制剂1-脱氧野尻霉素。为了制备作为糖基二酯酶I抑制剂的类似2-N-连接化合物1，得到了2-氨基-2-脱氧-D-葡萄糖苷的新型N-苯基衍生物11。
• Synthesis of C-terminal glycopeptides<i>via</i>oxime resin aminolysis
  作者：Thomas Tremblay、Gabrielle Robert-Scott、Christopher Bérubé、Antoine Carpentier、Normand Voyer、Denis Giguère

  DOI：10.1039/c9cc07481c

  日期：——

  Natural glycopeptides have been shown to possess interesting biological activities. In this work, we have developed a general solid-phase approach to C-terminal glycopeptides. Taking advantage of oxime resin ester bond nucleophile susceptibility, we optimised the nucleophilic cleavage step with glycosylamines and demonstrated the generality and scope of this method. In addition, this reaction has high

  天然糖肽已显示具有有趣的生物学活性。在这项工作中，我们已经开发出一种用于C端糖肽的通用固相方法。利用肟树脂酯键亲核试剂的敏感性，我们用糖胺优化了亲核裂解步骤，并证明了该方法的一般性和适用范围。此外，该反应具有较高的官能团耐受性，可用于制备更长的C端糖肽，一步法合成糖苷十二肽证明了这一点。结果为有效地获得新型医学相关化合物铺平了道路。
• Efficient and Catalyst-Free Michael Addition of d-Glucosamines to Acetylenic and Vinylic Compounds: Access to Vinylogous Carbamates of d-Glucosamine Derivatives
  作者：Rama Peddinti、Arun Sharma、Jyoti Agarwal、Naresh Kamatham

  DOI：10.1055/s-0034-1380676

  日期：——

  An efficient, catalyst-free methodology has been developed for the Michael addition reaction between d -glucosamine derivatives and various Michael acceptors. All reactions proceeded smoothly at room temperature to furnish novel sugar-derived vinylogous carbamates in high chemical yields and excellent stereoselectivity.

  已经为 d-葡糖胺衍生物和各种迈克尔受体之间的迈克尔加成反应开发了一种高效、无催化剂的方法。所有反应都在室温下顺利进行，以高化学产率和优异的立体选择性提供新型糖衍生的乙烯基氨基甲酸酯。
• Glucosamine-Based Primary Amines as Organocatalysts for the Asymmetric Aldol Reaction
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1021/jo1023156

  日期：2011.5.6

  Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexanone and aryl aldehydes having diversified substituents. Furthermore, the anomeric effect of various groups present at the anomeric position on the catalytic activity of these organocatalysts was also studied.