ethyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate | 399508-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
• CAS: 399508-48-6
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: HTZGTIDNENEORY-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate 在 二异丁基氢化铝 、 potassium iodide 、 silver(l) oxide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyacetaldehyde
  参考文献：
  名称：

  Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues

  摘要：

  The syntheses of the four imidazolo-piperidino-pentoses 3-6, which belong to the D-series, and of their L-enantiomers, ent-3 to ent-6, are reported. Ascorbic acid and isoascorbic acid were converted over several steps into the L-threo/L-erythro- and the D-erythro/D-threo-configured aldotetroses, respectively, which are the key building blocks for the eight target imidazolo-pentoses cited above. Nucleophilic addition of a metallated imidazole to any one of these four aldotetroses gave the corresponding two diastereomeric adducts, intramolecular cyclisation of which provided the expected bicyclic target molecules, with some protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight piperidinoses in Scheme 1 were determined unambiguously, by a combination of H-1/C-13 NMR spectroscopy, circular dichroism (CD) and MD values, in conjunction with single-crystal X-ray diffraction analyses of the L-arabino and D-lyxo azasugars ent-3 and 6. Although lacking the hydroxymethylene group in the C(5) position, the overall structure of these eight stereomers strongly resembles that of the natural product nagstatine (1), a potent inhibitor of N-acetyl-beta -D-glucosaminidase. As a matter of fact, after examination of the inhibitory properties of these imidazolo-piperidinoses against six commonly encountered glycosidases, we observe that the L-arabino imidazolo-sugar ent-3 is a potent inhibitor in this series, with K-i = 1 muM both with a beta -glucosidase and with a beta -galactosidase. The D-ribo and D-xylo stereomers 4 and 5 proved to be inhibitors of a beta -glucosidase of similar magnitude (4: K-i = 20 muM; 5: K-i = 17 muM), the other stereomers being either modest to poor inhibitors, or showing no inhibition at all.

  DOI：

  10.1002/1099-0690(200111)2001:21<4111::aid-ejoc4111>3.0.co;2-7
• 作为产物：
  描述：

  ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 在 吡啶 、 三氟甲磺酸酐 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到ethyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
  参考文献：
  名称：

  Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues

  摘要：

  The syntheses of the four imidazolo-piperidino-pentoses 3-6, which belong to the D-series, and of their L-enantiomers, ent-3 to ent-6, are reported. Ascorbic acid and isoascorbic acid were converted over several steps into the L-threo/L-erythro- and the D-erythro/D-threo-configured aldotetroses, respectively, which are the key building blocks for the eight target imidazolo-pentoses cited above. Nucleophilic addition of a metallated imidazole to any one of these four aldotetroses gave the corresponding two diastereomeric adducts, intramolecular cyclisation of which provided the expected bicyclic target molecules, with some protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight piperidinoses in Scheme 1 were determined unambiguously, by a combination of H-1/C-13 NMR spectroscopy, circular dichroism (CD) and MD values, in conjunction with single-crystal X-ray diffraction analyses of the L-arabino and D-lyxo azasugars ent-3 and 6. Although lacking the hydroxymethylene group in the C(5) position, the overall structure of these eight stereomers strongly resembles that of the natural product nagstatine (1), a potent inhibitor of N-acetyl-beta -D-glucosaminidase. As a matter of fact, after examination of the inhibitory properties of these imidazolo-piperidinoses against six commonly encountered glycosidases, we observe that the L-arabino imidazolo-sugar ent-3 is a potent inhibitor in this series, with K-i = 1 muM both with a beta -glucosidase and with a beta -galactosidase. The D-ribo and D-xylo stereomers 4 and 5 proved to be inhibitors of a beta -glucosidase of similar magnitude (4: K-i = 20 muM; 5: K-i = 17 muM), the other stereomers being either modest to poor inhibitors, or showing no inhibition at all.

  DOI：

  10.1002/1099-0690(200111)2001:21<4111::aid-ejoc4111>3.0.co;2-7

文献信息

• SUBSTITUTED BIARYL ALKYL AMIDES
  申请人：BioTheryX, Inc.

  公开号：US20130102649A1

  公开（公告）日：2013-04-25

  Disclosed herein are substituted biaryl alkyl amide compounds, methods of synthesizing substituted biaryl alkyl amide compounds and methods of treating diseases and/or conditions with substituted biaryl alkyl amide compounds.

  本文披露了替代的联苯烷基酰胺化合物，合成替代的联苯烷基酰胺化合物的方法，以及利用替代的联苯烷基酰胺化合物治疗疾病和/或症状的方法。
• US8822527B2
  申请人：——

  公开号：US8822527B2

  公开（公告）日：2014-09-02
• US9546131B2
  申请人：——

  公开号：US9546131B2

  公开（公告）日：2017-01-17
• [EN] SUBSTITUTED BIARYL ALKYL AMIDES<br/>[FR] AMIDES À BIARYLE ALKYLE SUBSTITUÉ
  申请人：BIOTHERYX INC

  公开号：WO2013059215A1

  公开（公告）日：2013-04-25

  Disclosed herein are substituted biaryl alkyl amide compounds, methods of synthesizing substituted biaryl alkyl amide compounds and methods of treating diseases and/or conditions with substituted biaryl alkyl amide compounds.
• Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues
  作者：François Gessier、Théophile Tschamber、Céline Tarnus、Markus Neuburger、Walter Huber、Jacques Streith

  DOI：10.1002/1099-0690(200111)2001:21<4111::aid-ejoc4111>3.0.co;2-7

  日期：2001.11

  The syntheses of the four imidazolo-piperidino-pentoses 3-6, which belong to the D-series, and of their L-enantiomers, ent-3 to ent-6, are reported. Ascorbic acid and isoascorbic acid were converted over several steps into the L-threo/L-erythro- and the D-erythro/D-threo-configured aldotetroses, respectively, which are the key building blocks for the eight target imidazolo-pentoses cited above. Nucleophilic addition of a metallated imidazole to any one of these four aldotetroses gave the corresponding two diastereomeric adducts, intramolecular cyclisation of which provided the expected bicyclic target molecules, with some protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight piperidinoses in Scheme 1 were determined unambiguously, by a combination of H-1/C-13 NMR spectroscopy, circular dichroism (CD) and MD values, in conjunction with single-crystal X-ray diffraction analyses of the L-arabino and D-lyxo azasugars ent-3 and 6. Although lacking the hydroxymethylene group in the C(5) position, the overall structure of these eight stereomers strongly resembles that of the natural product nagstatine (1), a potent inhibitor of N-acetyl-beta -D-glucosaminidase. As a matter of fact, after examination of the inhibitory properties of these imidazolo-piperidinoses against six commonly encountered glycosidases, we observe that the L-arabino imidazolo-sugar ent-3 is a potent inhibitor in this series, with K-i = 1 muM both with a beta -glucosidase and with a beta -galactosidase. The D-ribo and D-xylo stereomers 4 and 5 proved to be inhibitors of a beta -glucosidase of similar magnitude (4: K-i = 20 muM; 5: K-i = 17 muM), the other stereomers being either modest to poor inhibitors, or showing no inhibition at all.