geranyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside | 681153-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: geranyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside
• 英文别名: geranyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranoside；geranyl(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy)β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(2E)-3,7-dimethylocta-2,6-dienoxy]oxan-2-yl]methyl acetate
• CAS: 681153-36-6
• 化学式: C₂₄H₃₇NO₉
• 分子量: 483.559
• InChiKey: PFOSCBXRPVTDDF-XJQSYNDTSA-N

物化性质

• 沸点：
  604.9±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  geranyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 在 甲醇 、 乙酸(2,9-二甲基-1,10-菲咯啉)钯(II)二聚体双(三氟甲磺酸盐) 、 sodium methylate 、 对苯醌 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 生成 N-((2R,3S,5R,6R)-2-(((E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-5-hydroxy-6-(hydroxymethyl)-4-oxotetrahydro-2H-pyran-3-yl)acetamide
  参考文献：
  名称：

  [EN] 3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL
  [FR] COMPOSÉ 3'-CÉTOGLYCOSIDE POUR LA LIBÉRATION LENTE D'UN ALCOOL VOLATIL

  摘要：

  本发明涉及由式(I)定义的3'-酮基糖苷化合物及其用于控制释放醇，特别是显示驱虫效果的醇。它还涉及制备式(I)的3'-酮基糖苷化合物的方法。此外，它还涉及包含式(I)的3'-酮基糖苷化合物的组合物。它还涉及使用式(I)的3'-酮基糖苷化合物来控制释放醇。它还涉及使用这种组合物的方法。

  公开号：

  WO2021160670A1
• 作为产物：
  描述：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 geranyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] 3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL
  [FR] COMPOSÉ 3'-CÉTOGLYCOSIDE POUR LA LIBÉRATION LENTE D'UN ALCOOL VOLATIL

  摘要：

  本发明涉及由式(I)定义的3'-酮基糖苷化合物及其用于控制释放醇，特别是显示驱虫效果的醇。它还涉及制备式(I)的3'-酮基糖苷化合物的方法。此外，它还涉及包含式(I)的3'-酮基糖苷化合物的组合物。它还涉及使用式(I)的3'-酮基糖苷化合物来控制释放醇。它还涉及使用这种组合物的方法。

  公开号：

  WO2021160670A1

文献信息

• N-acetylglucosamine derivatives and use thereof
  申请人：Miura Kyoko

  公开号：US20060020127A1

  公开（公告）日：2006-01-26

  The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

  本发明涉及一种由以下式（1）表示的N-乙酰葡萄糖氨衍生物，以及含有该衍生物的透明质酸生产促进剂和皮肤外用制剂：其中R1是氢原子或具有2到18个碳原子的烷基；R2、R3和R4是氢原子或具有2到18个碳原子的酰基，可以全部相同或不同；位置1处的立体结构可以是α或β；前提是R1、R2、R3和R4不能全部是氢原子。本发明旨在提供一种容易获得的透明质酸生产促进剂和皮肤外用制剂，从而可以促进皮肤中透明质酸的产生，使皮肤保持活力和湿润状态，从而预防人类皮肤老化。
• N-ACETYGLUCOSAMINE DERIVATIVES AND USE THEREOF
  申请人：MIURA Kyoko

  公开号：US20080293673A1

  公开（公告）日：2008-11-27

  The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

  本发明涉及以下式（1）所表示的N-乙酰葡萄糖氨衍生物，以及含有该衍生物的透明质酸生产促进剂和皮肤外用制剂：其中，R1是氢原子或具有2至18个碳原子的烷基；R2、R3和R4是氢原子或具有2至18个碳原子的酰基，可以全部相同或不同；位置1的立体结构可以是α或β；前提是R1、R2、R3和R4不能全部是氢原子。旨在提供一种易于获得的透明质酸生产促进剂和皮肤外用制剂，通过促进皮肤中透明质酸的产生，从而使皮肤保持活力和湿润状态，预防人体皮肤老化。
• Synthesis of anti -inflammatory α-and β-linked acetamidopyranosides as inhibitors of toll-like receptor 4 (TLR4)
  作者：Peter Wipf、Benjamin R. Eyer、Yukihiro Yamaguchi、Feng Zhang、Matthew D. Neal、Chhinder P. Sodhi、Misty Good、Maria Branca、Thomas Prindle、Peng Lu、Jeffrey L. Brodsky、David J. Hackam

  DOI：10.1016/j.tetlet.2014.11.048

  日期：2015.6

  The low-molecular weight isopropyl 2-acetamido-alpha-glucoside 16 (C34) inhibits toll-like receptor 4 (TLR4) in enterocytes and macrophages in vitro, and reduces systemic inflammation in mouse models of endotoxemia and necrotizing enterocolitis. We used a copper(II)-mediated solvolysis of anomeric oxazolines and an acid-mediated conversion of beta-glucosamine and beta-galactosamine pentaacetates to generate analogs of 16 at the anomeric carbon and at C-4 of the pyranose ring. These compounds were evaluated for their influence on TLR4-mediated inflammatory signaling in cultured enterocytes and monocytes. Their efficacy was confirmed using a NF-kB-luciferase reporter mouse, thus establishing the first structure-activity relationship (SAR) study in this series and identifying the more efficacious isopropyl 2-acetamido-alpha-galactoside 17. (C) 2014 Elsevier Ltd. All rights reserved.
• N-ACETYLGLUCOSAMINE DERIVATIVES AND USE THEREOF
  申请人：KAO CORPORATION

  公开号：EP1553101B1

  公开（公告）日：2016-11-30
• US7393937B2
  申请人：——

  公开号：US7393937B2

  公开（公告）日：2008-07-01