ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-heptofuranuronate | 500908-09-8

• 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 [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-heptofuranuronate
• 英文别名: 3-Amino-3-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propionic acid, ethyl ester；ethyl 3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate
• CAS: 500908-09-8
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: HAOPMNGSBHHCGF-MOUFXGFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-heptofuranuronate 在 1H-咪唑-1-磺酰叠氮 、 copper(l) iodide 、 potassium carbonate 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  One-Pot Synthesis of Glycosyl-β-azido Ester via Diazotransfer Reaction Toward Access of Glycosyl-β-triazolyl Ester

  摘要：

  A concise and efficacious one-pot protocol for the synthesis of novel glycosyl-beta-azido ester 3 from glycosyl olefinic ester 1 under mild conditions has been devised. The beta-aminoester, formed by the conjugate addition of ammonia on olefinic ester, undergoes a metal-catalyzed diazotransfer reaction to furnish glycosyl-beta-azido ester. The optimized conditions for diazotransfer reaction indicate that imidazole-1-sulphonyl azide and K2CO3 give the best results in the presence of ZnCl2. A diverse range of novel regioselective triazolyl glycoconjugates 6a-u have been achieved in high yields via 1,3-dipolar cycloaddition of compound 3 with various alkynes in the presence of Cul/DIPEA. Structures of all the compounds have been elucidated using IR, NMR, MS, and elemental analysis, and four of them (3a, 3b, 4b, and 6a) have also been characterized by single crystal X-ray diffraction analysis.

  DOI：

  10.1021/acs.joc.5b00179
• 作为产物：
  描述：

  ethyl (5Z)-3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranuroate 在 氨 作用下， 以 乙醇 为溶剂， 生成 ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-heptofuranuronate
  参考文献：
  名称：

  Synthesis and bioevaluation of glycosyl ureas as α-glucosidase inhibitors and their effect on mycobacterium

  摘要：

  Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14-32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 Angstrom MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal (x-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity. (C) 2000 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00214-1

文献信息

• 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.
• Synthesis and DNA Topoisomerase-II Inhibitory Activity of Unnatural Nucleosides
  作者：Ram Chandra Mishra、Namrata Dwivedi、Iti Bansal、Jitendra Kumar Saxena、Rama Pati Tripathi

  DOI：10.1081/ncn-200046776

  日期：2005.1.1

  The synthesis and biological activities Of a number of unnatural nucleosides (23 - 43) is described. Nucleosides have been synthesized by SnCl4-catalyzed condensation of amino sugar acetates and silylated modified pyrimidines. Few of the 2'-O-acetyl derivatives of the nucleosides were hydrolyzed to the respective hydroxy derivatives 0 treatment with methanol saturated with ammonia. The compounds were screened against Filarial DNA-topoisomerase-II but on one of the compounds (29) inhibited this enzyme at 40 mug/mL of reaction mixture.
• One-Pot Synthesis of Glycosyl-β-azido Ester via Diazotransfer Reaction Toward Access of Glycosyl-β-triazolyl Ester
  作者：Amrita Mishra、Vinod K. Tiwari

  DOI：10.1021/acs.joc.5b00179

  日期：2015.5.15

  A concise and efficacious one-pot protocol for the synthesis of novel glycosyl-beta-azido ester 3 from glycosyl olefinic ester 1 under mild conditions has been devised. The beta-aminoester, formed by the conjugate addition of ammonia on olefinic ester, undergoes a metal-catalyzed diazotransfer reaction to furnish glycosyl-beta-azido ester. The optimized conditions for diazotransfer reaction indicate that imidazole-1-sulphonyl azide and K2CO3 give the best results in the presence of ZnCl2. A diverse range of novel regioselective triazolyl glycoconjugates 6a-u have been achieved in high yields via 1,3-dipolar cycloaddition of compound 3 with various alkynes in the presence of Cul/DIPEA. Structures of all the compounds have been elucidated using IR, NMR, MS, and elemental analysis, and four of them (3a, 3b, 4b, and 6a) have also been characterized by single crystal X-ray diffraction analysis.
• Synthesis and bioevaluation of glycosyl ureas as α-glucosidase inhibitors and their effect on mycobacterium
  作者：Neetu Tewari、V.K. Tiwari、R.C. Mishra、R.P. Tripathi、A.K. Srivastava、R. Ahmad、R. Srivastava、B.S. Srivastava

  DOI：10.1016/s0968-0896(03)00214-1

  日期：2003.7

  Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14-32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 Angstrom MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal (x-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity. (C) 2000 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Science Ltd. All rights reserved.