1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene | 184155-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene
• 英文别名: (2R,3S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-3-amine
• CAS: 184155-63-3
• 化学式: C₃₀H₃₅NO₄
• 分子量: 473.612
• InChiKey: YWDOOPWBZGUBQA-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene 在 吡啶 、 三氟化硼乙醚 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene
  参考文献：
  名称：

  Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine

  摘要：

  Attempts to synthesise alpha-C-glycosides of N-acetylgalactosamine by selective deprotection at C-2' of allyl alpha-C-galactoside 1 and subsequent amination failed, but opened the way to alpha-C-talopyranosides. The synthesis of alpha-C-glycosides of N-acetylgalactosamine was performed from allyl alpha-C-glucopyranoside 9, which was regioselectively deprotected, stereoselectively aminated at C-2', and finally epimerised at C-4'. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00480-2
• 作为产物：
  描述：

  3-C-(3,4,6-tri-O-benzyl-α-D-arabino-hex-2-ulopyranosyl)propene 在 盐酸 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 99.0h， 生成 1-(2'-amino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene
  参考文献：
  名称：

  New and Easy Access to C-Glycosides of Glucosamine and Mannosamine

  摘要：

  DOI：

  10.1021/jo970127f

文献信息

• Synthesis of Carbohydrate-Templated Amino Acids and Methods of Using Same
  申请人：Schweizer Frank

  公开号：US20080275213A1

  公开（公告）日：2008-11-06

  The present invention generally relates to tetrahydropyranyl-derivatized amino acids, their syntheses and their incorporation into peptides and peptidomimetics. The tetrahydropyran moiety constrains the side chain of an amino acid, thereby providing a molecule that may act as a sugar- or amino acid-mimetic as well as a scaffold for combinatorial synthesis.

  这项发明通常涉及四氢吡喃基衍生的氨基酸，它们的合成以及它们被纳入肽和肽类似物中。四氢吡喃基约束氨基酸的侧链，从而提供一种可能作为糖或氨基酸类似物的分子，同时也作为组合合成的支架。
• Tuning of the Prolyl <i>trans</i>/<i>cis</i>-Amide Rotamer Population by Use of <i>C</i>-Glucosylproline Hybrids
  作者：Neil W. Owens、Craig Braun、Frank Schweizer

  DOI：10.1021/jo0700833

  日期：2007.6.1

  describe the synthesis of a fused bicyclic C-glucosylproline hybrid (GlcProH) from commercially available 2,3,4,6-tetra-O-benzyl-d-glucopyranose. The GlcProH was incorporated into the model peptides Ac-GlcProH-NHMe and Ac-Gly-GlcProH-NHMe. Postsynthetic modifications can be introduced via derivatization of the carbohydrate scaffold. Conformational analysis of the GlcProH-modified model peptides shows that

  我们描述了稠合的双环的合成Ç由市售2,3,4,6-四-glucosylproline杂交体（GlcProH）ø -苄基- d -glucopyranose。将GlcProH掺入模型肽Ac-GlcProH-NHMe和Ac-Gly-GlcProH-NHMe中。合成后的修饰可以通过碳水化合物支架的衍生而引入。GlcProH修饰的模型肽的构象分析表明，尽管GlcProH的构象保持固定，但脯氨酸的N末端酰胺平衡（K t / c）可以随着碳水化合物支架的不同修饰而变化。通过NMR光谱研究的简单N-酰基衍生物表明，在CD 3中OD随着糖取代基由苄基（10％）变为羟基（22％）至乙酸酯（36％）而增加了顺酰胺含量。在DMSO- d 6中也观察到了类似的效果。影响的确切性质尚不清楚，但很可能是糖基与肽酰胺主链之间的分子内相互作用引起的。总体而言，我们的GlcProH通过调节碳水化合物支架展示了K t / c的变化：脯氨酸肽模拟物的新概念。
• [EN] C-GLYCOSIDES AS ANTI-INFLAMMATORY AGENTS<br/>[FR] C-GLYCOSIDES UTILISÉS COMME AGENTS ANTI-INFLAMMATOIRES
  申请人：[en]UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：WO2024010959A1

  公开（公告）日：2024-01-11

  Novel compounds and methods of using the compounds are provided herein. The compounds include novel carbon analogs of pyranose derivatives discovered to have Toll- like receptor 4 (Tlr4) inhibitory activity. The methods provide for treating infectious, inflammatory and post-traumatic disorders.
• Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine
  作者：Laura Cipolla、Barbara La Ferla、Luigi Lay、Francesco Peri、Francesco Nicotra

  DOI：10.1016/s0957-4166(99)00480-2

  日期：2000.1

  Attempts to synthesise alpha-C-glycosides of N-acetylgalactosamine by selective deprotection at C-2' of allyl alpha-C-galactoside 1 and subsequent amination failed, but opened the way to alpha-C-talopyranosides. The synthesis of alpha-C-glycosides of N-acetylgalactosamine was performed from allyl alpha-C-glucopyranoside 9, which was regioselectively deprotected, stereoselectively aminated at C-2', and finally epimerised at C-4'. (C) 2000 Elsevier Science Ltd. All rights reserved.
• New and Easy Access to C-Glycosides of Glucosamine and Mannosamine
  作者：Laura Cipolla、Luigi Lay、Francesco Nicotra

  DOI：10.1021/jo970127f

  日期：1997.9.1