4-methylphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside | 35695-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: p-tolyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside；p-tolyl-2-deoxy-2-acetamido-1-thio-D-glucopyranoside；4-Methylphenyl 2-(acetylamino)-2-deoxy-1-thio-I(2)-D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-methylphenyl)sulfanyloxan-3-yl]acetamide
• CAS: 35695-00-2
• 化学式: C₁₅H₂₁NO₅S
• 分子量: 327.401
• InChiKey: ZPGAGRMBPHPYHR-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside 在 甲醇 、 N-碘代丁二酰亚胺 、 calcium hydride 、 D(+)-10-樟脑磺酸 、 水 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 6.17h， 生成 methyl N-acetyl-2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl(1→3)-2,6-di-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  一类氨基葡萄糖给体及其应用

  摘要：

  本发明公开了一类氨基葡萄糖给体及其应用，该氨基葡萄糖给体在C‑2位置氮原子引入N,N‑二乙酰基保护，并在氨基葡萄糖C‑3、C‑4、C‑6最少一个位置引入富电子的活化(armed)保护基，其中N,N‑二乙酰基具有邻基参与作用，能够生成单一β选择性的糖苷化产物，并且在甲醇/甲醇钠等较温和条件下与其他位置酰基一釜法脱除，提高合成效率。该类氨基葡萄糖给体的异头位离去基团可以为卤素、硫苷、亚胺酯、戊烯烷氧基、羟基等，并且能够与不同受体反应构建β糖苷键，反应效率高。

  公开号：

  CN111925403A
• 作为产物：
  描述：

  D-GlcNAc 在 甲醇 、 molybdenum(VI) oxychloride 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 4-methylphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

  摘要：

  Among five different oxidometallic species and two Lewis acids investigated, MoO(2)Cl(2) shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.024

文献信息

• Reinvestigation of <i>N</i>,<i>N</i>-Diacetylimido-Protected 2-Aminothioglycosides in <i>O</i>-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation
  作者：Liming Shao、Zhenni Huo、Na Lei、Min Yang、Zehuan He、Yongliang Zhang、Qinlong Wei、Changsheng Chen、Mei Xiao、Fei Wang、Guofeng Gu、Feng Cai

  DOI：10.1021/acs.joc.1c01009

  日期：2021.10.1

  N,N-Diacetylimido protection of 2-aminoglycosides is an elegant strategy but has had limited applications due to unexpected side reactions in glycosylation. We found that high acid concentrations could diminish the side reactions. We observed intermolecular hydrogen bonding among alcohols and acids could disrupt. Assuming that intermolecular hydrogen bonding accelerates the formation of 1,2-orthoamides

  2-氨基糖苷的N , N-二乙酰亚氨基保护是一种优雅的策略，但由于糖基化中的意外副反应而应用有限。我们发现高酸浓度可以减少副反应。我们观察到醇和酸之间的分子间氢键可能会破坏。假设分子间氢键加速了 1,2-邻酰胺的形成并且破坏分子间氢键可以转变为所需的糖基化，我们成功地在范围广泛的醇受体的糖基化中以及在一个一锅合成受保护的人乳寡糖，乳-N-新四糖。
• A closer look at ligand specificity for cellular activation of NOD2 with synthetic muramyl dipeptide analogues
  作者：Christopher Adamson、Yaquan Liang、Shiliu Feng、Allan Wee Ren Ng、Yuan Qiao

  DOI：10.1039/d3cc05807g

  日期：——

  To further understand the specificity of muramyl dipeptide (MDP) sensing by NOD2, we evaluated the compatibility of synthetic MDP analogues for cellular uptake and NAGK phosphorylation, the pre-requisite steps of intracellular NOD2 activation.

  为了进一步了解 NOD2 对氨甲酰二肽（MDP）感应的特异性，我们评估了合成 MDP 类似物对细胞摄取和 NAGK 磷酸化的兼容性，这是细胞内 NOD2 激活的前提步骤。
• 10.1007/s11171-008-2012-0
  作者：Zemlyakov、Tsikalova、Azizova、Chirva、Mulik、Shkalev、Kalyuzhin、Kiselevsky

  DOI：10.1007/s11171-008-2012-0

  日期：——
• A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and aryl thiols or disulfides
  作者：Keith A. Stubbs、Matthew S. Macauley、David J. Vocadlo

  DOI：10.1016/j.carres.2005.12.009

  日期：2006.7

  An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly furnishes crystalline materials in good yields. The procedure is compatible with a range of thiols and disulfides and may be amenable for preparing a wide range of thioglycosides with various glycons and aglycons. (c) 2006 Elsevier Ltd. All rights reserved.
• A green and regioselective acetylation of thioglycoside with ethyl acetate
  作者：Pi-Hui Liang、Yin-Jen Lu、Ting-Hsuan Tang

  DOI：10.1016/j.tetlet.2010.10.135

  日期：2010.12

  Treatment of saccharidic polyols in ethyl acetate with catalytic sulfuric acid leads to the corresponding primary monoacetate derivatives in good yields. The transesterification was realized by simple stirring without rigorous exclusion of moisture or oxygen. Our protocol is applicable to the regioselective mono-acetylation of amino sugars having different substituents at the 2-positions. (C) 2010 Elsevier Ltd. All rights reserved.