ethyl [3-O-methyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate | 500908-10-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl [3-O-methyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate
• 英文别名: ethyl [5-benzylamino-5,6-dideoxy]-1,2-O-isopropylidene-3-O-methyl-β-L-ido-heptofuranuronate；ethyl 3-O-methyl-5-(benzylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate；ethyl (3R)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(benzylamino)propanoate
• CAS: 500908-10-1
• 化学式: C₂₀H₂₉NO₆
• 分子量: 379.453
• InChiKey: LWSUYTSBYPLYDM-IQZDNPOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl [3-O-methyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate 在 4 A molecular sieve 、 四丁基溴化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (6S)-1-benzyl-3-(4-chlorophenyl)-5,6-dihydro-6-(1,2-O-isopropylidene-3-O-methyl-α-D-xylo-tetrafuranos-4-yl)uracil
  参考文献：
  名称：

  A Versatile Synthesis of DihydropyrimidinoneC‐Nucleosides

  摘要：

  A versatile synthesis of N-substituted dihydropyrimidinone C-nucleosides (20-29) is described. Glycosyl amino esters (3-9), obtained by reductive alkylation of glycosyl amino esters 1 and 2, on condensation with different isocyanates afforded respective ureido derivatives (10-19) in good to quantitative yields. The latter on cyclative amidation with a combination of DBU/TBAB (tetrabutylammonium bromide)/4Angstrom molecular sieve gave the corresponding nucleosides (20-29) in good yields.

  DOI：

  10.1081/ncn-120030712
• 作为产物：
  描述：

  1,2-O-异亚丙基-3-O-甲基-Alpha-D-木五二呋喃醛糖-(1,4) 以 乙醇 、 甲苯 为溶剂， 生成 ethyl [3-O-methyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate
  参考文献：
  名称：

  CONJUGATE ADDITION OF AMINES TO SUGAR DERIVED OLEFINIC ESTERS: SYNTHESIS OF GLYCOSYLATED AMINO ESTERS AS DNA TOPOISOMERASE-II INHIBITORS

  摘要：

  Conjugate addition of amines to olefinic esters derived from sugars leading to formation of glycosylated amino esters in a stereoselective manner is described. Some of the synthesized compounds possess DNA topoisomerase-II enzyme inhibitory activities at low concentrations.

  DOI：

  10.1081/car-120016857

文献信息

• Synthesis and Antitubercular Evaluation of Diverse Glycosylated Ureas from D-Glucose
  作者：Neetu Tripathi、Vinod K. Tiwari

  DOI：10.1155/2024/8709672

  日期：2024.2.2

  N, N-disubstituted glycosylated ureas have been synthesized in good-to-excellent yields by 1,4-conjugate addition of amines to glycosylated olefinic esters followed by reaction of resulting glycosyl β-amino esters with diisocyanates. The developed sugar-based molecules were well characterized by extensive standard spectroscopic analysis including NMR (1H, 13C, and DEPT), IR, MS, and elemental analysis

  通过将胺1,4-共轭加成到糖基化烯酯上，然后将所得糖基β-氨基酯与二异氰酸酯反应，以良好至优异的产率合成了N,N-二取代的糖基化脲。所开发的糖基分子通过广泛的标准光谱分析（包括 NMR（1 H、13 C 和 DEPT）、IR、MS 和元素分析）得到了很好的表征，并筛选了其抗结核分枝杆菌( M. Tb. )的生物活性。 ，其中一些表现出有效的抗结核活性。这些分子的设计考虑了参与分枝杆菌细胞壁聚合物生物合成的众所周知的酶抑制剂，并且可以作为先导分子进一步探索，以成功开发潜在的抗结核候选药物。
• Synthesis of glycosylated β-amino acids as new class of antitubercular agents
  作者：R.P. Tripathi、R. Tripathi、V.K. Tiwari、Laxmi Bala、S Sinha、A. Srivastava、R. Srivastava、B.S. Srivastava

  DOI：10.1016/s0223-5234(02)01398-3

  日期：2002.9

  A series of glycosylated P-amino acids was prepared and evaluated against Mycohacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the biosynthesis of essential cell wall peptidoglycan and arabinogalactan. Though most of the compounds exhibited little activity, however, one showed significant activity against all the strains in cell culture and activity was confirmed by BACTEC method. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• CONJUGATE ADDITION OF AMINES TO SUGAR DERIVED OLEFINIC ESTERS: SYNTHESIS OF GLYCOSYLATED AMINO ESTERS AS DNA TOPOISOMERASE-II INHIBITORS
  作者：A. Khan、R. Tripathi、V. Tiwari、R. Mishra、V.J. Reddy、J. Saxena

  DOI：10.1081/car-120016857

  日期：——

  Conjugate addition of amines to olefinic esters derived from sugars leading to formation of glycosylated amino esters in a stereoselective manner is described. Some of the synthesized compounds possess DNA topoisomerase-II enzyme inhibitory activities at low concentrations.
• A Versatile Synthesis of Dihydropyrimidinone<i>C</i>‐Nucleosides
  作者：Ram Chandra Mishra、Diksha Katiyar、Neetu Tewari、Rama Pati Tripathi

  DOI：10.1081/ncn-120030712

  日期：2004.12.31

  A versatile synthesis of N-substituted dihydropyrimidinone C-nucleosides (20-29) is described. Glycosyl amino esters (3-9), obtained by reductive alkylation of glycosyl amino esters 1 and 2, on condensation with different isocyanates afforded respective ureido derivatives (10-19) in good to quantitative yields. The latter on cyclative amidation with a combination of DBU/TBAB (tetrabutylammonium bromide)/4Angstrom molecular sieve gave the corresponding nucleosides (20-29) in good yields.