(1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol

被引:1
作者
Fortunato, Milene A. G. [1 ]
Siopa, Filipa [1 ]
Afonso, Carlos A. M. [1 ]
机构
[1] Univ Lisbon, Res Inst Med iMed ULisboa, Fac Pharm, Av Prof Gama Pinto, P-1649003 Lisbon, Portugal
关键词
aminocyclopentitol; bicyclic aziridine; water chemistry; nucleophilic substitution; PYRIDINIUM SALT PHOTOCHEMISTRY; AMINOCYCLOPENTITOLS; AZIRIDINES; INHIBITOR; VERSATILE; CYP51;
D O I
10.3390/M1199
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio) cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via H-1, C-13-NMR, HSQC, and mass spectral data.
引用
收藏
页数:5
相关论文
共 23 条
  • [11] Convenient syntheses of orthogonally protected aminocyclopentitols from aldopentoses
    Kosak, Urban
    Hrast, Martina
    Knez, Damijan
    Maras, Nenad
    Crnugelj, Martin
    Gobec, Stanislav
    [J]. TETRAHEDRON LETTERS, 2015, 56 (03) : 529 - 531
  • [12] A demonstration of the synthetic potential of pyridinium salt photochemistry by its application to a stereocontrolled synthesis of (+)-mannostatin A
    Ling, R
    Mariano, PS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) : 6072 - 6076
  • [13] Exploratory investigations probing a preparatively versatile, pyridinium salt photoelectrocyclization-solvolytic aziridine ring opening sequence
    Ling, R
    Yoshida, M
    Mariano, PS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) : 4439 - 4449
  • [14] The Investigational Fungal Cyp51 Inhibitor VT-1129 Demonstrates Potent In Vitro Activity against Cryptococcus neoformans and Cryptococcus gattii
    Lockhart, Shawn R.
    Fothergill, Annette W.
    Iqbal, Naureen
    Bolden, Carol B.
    Grossman, Nina T.
    Garvey, Edward P.
    Brand, Stephen R.
    Hoekstra, William J.
    Schotzinger, Robert J.
    Ottinger, Elizabeth
    Patterson, Thomas F.
    Wiederhold, Nathan P.
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2016, 60 (04) : 2528 - 2531
  • [15] Aza-Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D
    Marin, Lucile
    Force, Guillaume
    Gandon, Vincent
    Schulz, Emmanuelle
    Leboeuf, David
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (33) : 5323 - 5328
  • [16] Palladium-catalyzed allylic substitution between C-based nucleophiles and 6-azabicyclo[3.1.0]-hex-3-en-2-oxy derivatives: A new selectivity paradigm
    Oliveira, Joao A. C.
    Kiala, Gredy
    Siopa, Filipa
    Bernard, Aurelie
    Gontard, Geoffrey
    Oble, Julie
    Afonso, Carlos A. M.
    Poli, Giovanni
    [J]. TETRAHEDRON, 2020, 76 (51)
  • [17] Flow-Assisted Synthesis of Bicyclic Aziridines via Photochemical Transformation of Pyridinium Salts
    Siopa, Filipa
    Antonio, Joao P. M.
    Afonso, Carlos A. M.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (04) : 551 - 556
  • [18] Stereoselective synthesis of polyhydroxylated indolizidines based on pyridinium salt photochemistry and ring rearrangement metathesis
    Song, L
    Duesler, EN
    Mariano, PS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (21) : 7284 - 7293
  • [19] Aziridines: epoxides' ugly cousins?
    Sweeney, JB
    [J]. CHEMICAL SOCIETY REVIEWS, 2002, 31 (05) : 247 - 258
  • [20] Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions
    Vale, Joao R.
    Siopa, Filipa
    Branco, Paula S.
    Afonso, Carlos A. M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (11) : 2048 - 2053