cyclohexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside | 21559-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-cyclohexyloxyoxan-2-yl]methyl acetate
• CAS: 21559-74-0
• 化学式: C₂₀H₃₁NO₉
• 分子量: 429.467
• InChiKey: SBJACEBXNZEQNU-WAPOTWQKSA-N

物化性质

• 沸点：
  570.8±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  cyclohexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  Hexyl, octyl, and cyclohexyl beta-glycosides and heptyl and cyclohexyl alpha-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP alpha-glycosides in comparison with the corresponding beta-glycosides and MDP itself. In the case of alkyl beta-glycosides, differences in hydrocarbon chain lengths (C-4-C-8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.

  DOI：

  10.1023/a:1023944818406
• 作为产物：
  描述：

  2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 在 1H-1,2,4-三唑 、 三氟甲磺酸三甲基硅酯 、 双氧水 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 cyclohexyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  New α-selective thermal glycosylation of acetyl-protected 2-acetamido-2-deoxy-β-d-glucopyranosyl diphenylphosphinate

  摘要：

  This paper describes new alpha-selective thermal glycosylation using acetyl-protected 2-acetamido-2-deoxy-beta-D-glucopyranosyl diphenylphosphinate (4) as a glycosyl donor. When the glycosylation of 4 with 1-hexanol was carried out under Various conditions, the conditions using trimethylsilyl trifluoromethanesulfonate as a promoter in nitromethane at reflux temperature were most suitable for the formation of the alpha anomer. The glycosylation of 4 with the other common alcohols gave corresponding alpha-glycosides in relatively high yields under the conditions. When cholesterol, a very steric hindered alcohol, was used as a glycosyl acceptor, alpha-glycoside was also produced predominantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00069-0

文献信息

• Studies of the stereoselective reduction of 2-hydroxyimino-hexopyranosides: LiBH4-Me3SiCl, a mild reducing agent of oximes to amines
  作者：Anna Banaszek、Wojciech Karpiesiuk

  DOI：10.1016/0008-6215(94)84288-4

  日期：1994.1

  Abstract Reduction of the title compounds of types 1 and 2 under mild conditions using LiBH 4 -Me 3 SiCl species, followed by acetylation, yielded the corresponding 2-amino sugars of α- d - gluco ( 5 ) and β- d - manno ( 6 ) configuration, respectively, with full stereoselectivity. Analogousy, the β- d - lyxo isomer of type 4 afforded the β- d -talosamine 9 exclusively. The stereochemical outcome of

  摘要使用LiBH 4 -Me 3 SiCl物种在温和条件下还原1型和2型标题化合物，然后进行乙酰化，得到相应的2-氨基糖α-d-葡萄糖（5）和β-d-甘露糖（ 6）配置，分别具有完全的立体选择性。类似地，类型4的β-d-lyxo异构体仅提供了β-d-塔洛糖胺9。3型肟还原的立体化学结果受底物的构型和C-1-C-4取代基的化学特征控制，从而导致talo（8）和/或galacto（7）异构体。
• Compositions and methods for treatment of inflammatory disorders
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US10668092B2

  公开（公告）日：2020-06-02

  The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier.

  本发明涉及通过施用新发现的具有 TLR4 抑制活性的各种化合物来治疗感染性、炎症性和创伤后疾病的方法。除治疗方法外，本发明还进一步提供了药物组合物，其中包含上述化合物以及合适的药物载体。
• Zemlyakov; Kur'yanov; Sidorova, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 551 - 558
  作者：Zemlyakov、Kur'yanov、Sidorova、Chirva

  DOI：——

  日期：——
• 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.
• Zemlyakov; Kur'yanov; Tsikalov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 6, p. 393 - 397
  作者：Zemlyakov、Kur'yanov、Tsikalov、Chirva

  DOI：——

  日期：——