3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose | 121123-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose
• 英文别名: 3,4,6-tri-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside；2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranose；2-(Acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-alpha-D-glucopyranose；N-[(2S,3R,4R,5S,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 121123-45-3
• 化学式: C₂₉H₃₃NO₆
• 分子量: 491.584
• InChiKey: BMOPHWKYXVHVMF-JPHCZMGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-O,2-N-(ethan-1-yl-1-ylidene)-α-D-glucopyranose
  参考文献：
  名称：

  2-乙酰氨基-2-脱氧糖基供体在低温下的糖基化：非恶唑啉法的范围

  摘要：

  研究了1，2-反式-β-连接的2-乙酰氨基-2-脱氧糖苷的直接构建。3,4,6-三-O-苄基和3,4,6-三-O-乙酰基保护的糖基二乙基亚磷酸酯和4,6 - O-亚苄基保护的半乳糖基亚磷酸二乙酯分别与多种受体反应化学计算量的Tf 2 NH在CH 2 Cl 2中存在的醇在-78°C的条件下，以完全高的立体选择性提供高至高收率的相应β-糖苷。一些实验提供了有力的证据，表明相应的恶唑啉鎓离子不负责该反应。我们证明了与相应的亚糖基亚氨酸酯和硫代糖苷的糖基化作用也在低温下进行，表明这些供体是亚磷酸酯的有吸引力的替代物的可能性。基于用2-乙酰氨基-2-脱氧甘露糖基供体获得的结果，提出了一种合理的反应机理，该机理以糖基三氟酰亚胺和接触离子对为反应性中间体。

  DOI：

  10.1021/acs.joc.5b00138
• 作为产物：
  描述：

  D-GlcNAc 在 palladium on activated charcoal barium hydroxide 、 甲酸铵 、 barium(II) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.27h， 生成 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose
  参考文献：
  名称：

  Stereospecific synthesis of C-(2-amino-2-deoxy-β-d-glucosyl) compounds by Wittig-type olefination of d-glucosamine derivatives

  摘要：

  DOI：

  10.1016/0008-6215(93)84048-b

文献信息

• Synthesis of Novel Donor Mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as Potential Transferase Inhibitors
  作者：Andreas Schäfer、Joachim Thiem

  DOI：10.1021/jo990766l

  日期：2000.1.1

  For the enzymatic transfer of galactose, N-acetylglucosamine, and N-acetylgalactosamine, UDP-Gal (1), UDP-GlcNAc (2), and UDP-GalNAc (3) are employed, and UDP serves as a feedback inhibitor. In this paper the synthesis of the novel UDP-sugar analogues 4, 5, and 6 as potential transferase inhibitors is described. Compounds 4-6 feature C-glycosidic hydroxymethylene linkages between the sugar and nucleoside

  对于半乳糖，N-乙酰氨基葡糖和N-乙酰半乳糖胺的酶促转移，使用UDP-Gal（1），UDP-GlcNAc（2）和UDP-GalNAc（3），并且UDP用作反馈抑制剂。在本文中，描述了作为潜在转移酶抑制剂的新型UDP-糖类似物4、5和6的合成。与天然衍生物1-3中的异头氧相反，化合物4-6在糖和核苷部分之间具有C-糖苷羟基亚甲基键。
• Formation of 2-Acetamido-2-deoxy-D-glucopyranosidic Linkages via Glycosidation Using a Combination of Two Lewis Acids
  作者：Takashi Yamanoi、Yoshiki Oda、Masanobu Midorikawa

  DOI：10.3987/com-14-s(k)4

  日期：——

  A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzy1-2-deoxy-alpha-D-glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-D-glucopyranosides in good yields with significant formation of the alpha-isomers. Notably, stereoselective glycosylations of phenol derivatives as the acceptors afforded aryl 1,2-cis-alpha-glycosides without the formation of any beta-isomers. This highly stereocontrolled 1,2-cis-alpha-glycosidation was applied to the synthesis of a novel hydroquinone alpha-glycoside.
• Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates
  作者：Nigel Kevin Jalsa

  DOI：10.1016/j.tetlet.2011.09.130

  日期：2011.12

  A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, groups which are normally labile under typical hydrogenolysis conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of acceptor substrate analogs for the study of glycosyltransferases involved in the second step of the biosynthesis of O-antigen repeating units
  作者：John G. Riley、Changchang Xu、Inka Brockhausen

  DOI：10.1016/j.carres.2009.12.022

  日期：2010.3

  O-antigens of Gram negative bacteria are polysaccharides covalently attached to lipopolysaccharides (LPS) that have roles as virulence factors. Due to the lack of defined substrates for in vitro assays only a few of the enzymes involved in the biosynthesis of O-antigens have been studied. Many O-antigens have GlcNAc at the reducing end of the oligosaccharide chain linked to pyrophosphate-lipid. We therefore designed and synthesized a series of GlcNAc-pyrophosphate-lipid analogs of the natural GlcNAc-pyrophosphate-undecaprenol acceptor substrate for studies of the acceptor specificities of O-antigen biosynthetic enzymes. We synthesized analogs with modifications of the pyrophosphate bond as well as the lipid chain. These compounds will be useful for the specificity studies of many bacterial glycosyltransferases. Knowledge of the substrate specificities is the basis for the development of specific glycosyltransferase inhibitors that could block O-antigen biosynthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• Iminosugar C-Glycoside Analogues of α-<scp>d</scp>-GlcNAc-1-Phosphate: Synthesis and Bacterial Transglycosylase Inhibition
  作者：Che-Hsiung Hsu、Mathias Schelwies、Sebastian Enck、Lin-Ya Huang、Shih-Hsien Huang、Yi-Fan Chang、Ting-Jen Rachel Cheng、Wei-Chieh Cheng、Chi-Huey Wong

  DOI：10.1021/jo501340s

  日期：2014.9.19

  We herein describe the first synthesis of iminosugar C-glycosides of α-D-GlcNAc-1-phosphate in 10 steps starting from unprotected D-GlcNAc. A diastereoselective intramolecular iodoamination-cyclization as the key step was employed to construct the central piperidine ring of the iminosugar and the C-glycosidic structure of α-D-GlcNAc. Finally, the iminosugar phosphonate and its elongated phosphate analogue were accessed. These phosphorus-containing iminosugars were coupled efficiently with lipophilic monophosphates to give lipid-linked pyrophosphate derivatives, which are lipid II mimetics endowed with potent inhibitory properties toward bacterial transglycosylases (TGase).