(1R,2R,3S,4R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate | 500908-12-3

• 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: (1R,2R,3S,4R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate
• 英文别名: ethyl 3-O-benzyl-5-(butylamino)-5,6-dideoxy-1,2-O-isopropylidene-heptofuranuronate；ethyl [3-O-benzyl-5,6-dideoxy-5-butylamino-1,2-O-isopropylidene]-heptofuranuronate；ethyl 3-[(3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(butylamino)propanoate；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-(butylamino)propanoate
• CAS: 500908-12-3
• 化学式: C₂₃H₃₅NO₆
• 分子量: 421.534
• InChiKey: DFDUOCZCTBFEKT-UAHLEYORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (1R,2R,3S,4R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-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 6.5h， 生成 (1'R,2'R,3'S,4'R,6S)-N¹-butyl-N³-(4-fluorophenyl)-5,6-dihydro-(1',2'-O-isopropylidene-3'-O-benzyl-1',2',3',4'-tetrahydrofuranos-4'-yl)pyrimidin-2,4-dione
  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
• 作为产物：
  描述：

  正丁胺 、 (1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate 以 乙醇 为溶剂， 以90%的产率得到(1R,2R,3S,4R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate
  参考文献：
  名称：

  在光信反应条件下方便合成新型糖基氮杂环丁烷

  摘要：

  摘要 以糖基β-氨基醇为原料，在Mitsunobu 反应条件下进行分子内环化，建立了一种简便、高产的合成新型糖基氮杂环丁烷的方案。图形概要

  DOI：

  10.1080/00397911.2011.587079

文献信息

• A Convenient Synthesis of Novel Glycosyl Azetidines Under Mitsunobu Reaction Conditions
  作者：Archana Singh、Bhuwan B. Mishra、Raju R. Kale、Divya Kushwaha、Vinod K. Tiwari

  DOI：10.1080/00397911.2011.587079

  日期：2012.12.15

  Abstract A facile, simple, and high-yielding protocol for synthesis of novel glycosyl azetidines was developed from glycosyl β-amino alcohols via intramolecular cyclization under Mitsunobu reaction conditions. GRAPHICAL ABSTRACT

  摘要 以糖基β-氨基醇为原料，在Mitsunobu 反应条件下进行分子内环化，建立了一种简便、高产的合成新型糖基氮杂环丁烷的方案。图形概要
• 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.