(1R,2R,3S,4R,5R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate | 517877-04-2

• 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,5R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate
• 英文别名: ethyl 1,2-O-isopropylidene-3-O-benzyl-5-(N-butylamino)-5,6-dideoxy-α-D-gluco-heptofuranuronate；ethyl 3-O-benzyl-5-(butylamino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-heptofuranuronate；ethyl [3-O-benzyl-5,6-dideoxy-5-butylamino-1,2-O-isopropylidene]-α-D-gluco-heptofuranuronate；ethyl (3R)-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: 517877-04-2
• 化学式: C₂₃H₃₅NO₆
• 分子量: 421.534
• InChiKey: DFDUOCZCTBFEKT-MIUGBVLSSA-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,5R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-α-D-gluco-heptofuranuronate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-3-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-butylamino-propan-1-ol
  参考文献：
  名称：

  Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-d-gluco-homonojirimycin and N-butyl 1-deoxy-l-ido-homonojirimycin

  摘要：

  Conjugate addition of n-butyl amine to D-glucose derived alpha,beta-unsaturated ester 4 afforded P-amino esters 5a,b that on reduction of ester group,. 1,2-acetonide deprotection, and reductive amination led to the formation of corresponding N-butyl 1-deOXY-D-gluco-homonojirimycin 2c and N-butyl 1-deOXY-L-ido-homonojirimycin 2d which were found to be selective P-glucosidase inhibitors with an IC50 value in millimolar range. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.027
• 作为产物：
  描述：

  3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 以 乙醇 、 甲苯 为溶剂， 生成 (1R,2R,3S,4R,5R)-ethyl [3-O-benzyl-5-butylamino-5,6-dideoxy-1,2-Oisopropylidene]-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

• 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 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.
• Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-d-gluco-homonojirimycin and N-butyl 1-deoxy-l-ido-homonojirimycin
  作者：Shankar D. Markad、Narayan S. Karanjule、Tarun Sharma、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.bmc.2006.04.027

  日期：2006.8

  Conjugate addition of n-butyl amine to D-glucose derived alpha,beta-unsaturated ester 4 afforded P-amino esters 5a,b that on reduction of ester group,. 1,2-acetonide deprotection, and reductive amination led to the formation of corresponding N-butyl 1-deOXY-D-gluco-homonojirimycin 2c and N-butyl 1-deOXY-L-ido-homonojirimycin 2d which were found to be selective P-glucosidase inhibitors with an IC50 value in millimolar range. (c) 2006 Elsevier Ltd. All rights reserved.