메뉴 건너뛰기




Volumn , Issue 13, 2007, Pages 2069-2072

Simple modifications of enantiopure 1,2-oxazines leading to building blocks for carbohydrate and peptide mimetics

Author keywords

1,3 dipolar cycloadditions; Carbohydrates; Oxidations; Peptides; Pyrans; Sugar amino acids

Indexed keywords

1,2 OXAZINE DERIVATIVE; ALKYNE; AZIDE; BETA LACTAM; CARBOHYDRATE; DIPEPTIDE; PEPTIDE; PYRAN; TRIAZOLE;

EID: 34548165069     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984907     Document Type: Article
Times cited : (28)

References (32)
  • 2
    • 34548172190 scopus 로고    scopus 로고
    • Angew. Chem. 2001, 113, 1624.
    • (2001) Chem , vol.113 , pp. 1624
    • Angew1
  • 5
    • 34548173439 scopus 로고    scopus 로고
    • Angew. Chem. 2002, 114, 240.
    • (2002) Chem , vol.114 , pp. 240
    • Angew1
  • 9
    • 33846509764 scopus 로고    scopus 로고
    • Angew. Chem. 2005, 117, 6383.
    • (2005) Chem , vol.117 , pp. 6383
    • Angew1
  • 10
    • 34548172683 scopus 로고    scopus 로고
    • Dissertation; Freie Universität: Berlin
    • Al-Harrasi, A. Dissertation; Freie Universität: Berlin, 2005.
    • (2005)
    • Al-Harrasi, A.1
  • 11
    • 34548186404 scopus 로고    scopus 로고
    • Compound 4b is obtained by the reduction of the corresponding TBS-protected ketone (see ref. 3) followed by protection of the secondary alcohol with BnBr.
    • Compound 4b is obtained by the reduction of the corresponding TBS-protected ketone (see ref. 3) followed by protection of the secondary alcohol with BnBr.
  • 12
    • 34548175191 scopus 로고    scopus 로고
    • Typical Procedure for the Conversion of 5 into 6 Alcohol 5 (0.320 g, 0.629 mmol) was dissolved in anhyd DMF (10 mL, then PDC (0.946 g, 2.52 mmol) and Ac2O (0.24 mL, 2.5 mmol) were added. The mixture was stirred for 12 h at r.t. Then, Et2O and H2O were added and the layers were separated. The organic layer was successively washed with H2O, dried (MgSO4, and the solvent was removed under reduced pressure. Purification by column chromatography (silica gel, hexane-EtOAc, 4:1 to 1:1) yielded 0.250 g (79, of 6 as a colorless solid. Analytical Data for tert-Butyl (1S,4S,5R,8S)-8-Benzyloxy-4-(tert-buryl-dimethylsiloxymethyl)-2,2-dimethyl-7-oxo-3-oxa-6- azabicyclo[3.2.1]octane-6-carboxylate (6, α]D22 +14.1 (c 1.43, CHCl3, mp 64-65°C. 1H NMR 500 MHz, CDC
    • 6Si (505.3): C, 64.12; H, 8.57; N, 2.77. Found: C, 64.22; H, 8.75; N, 2.78.
  • 17
    • 34548146542 scopus 로고
    • Angew. Chem. 1963, 75, 604.
    • (1963) Chem , vol.75 , pp. 604
    • Angew1
  • 19
    • 0013064237 scopus 로고    scopus 로고
    • Angew. Chem. 2002, 114, 2708.
    • (2002) Chem , vol.114 , pp. 2708
    • Angew1
  • 22
    • 34548178500 scopus 로고    scopus 로고
    • 3 is not explosive and is stable at r.t.
    • 3 is not explosive and is stable at r.t.
  • 24
    • 34548145106 scopus 로고    scopus 로고
    • Typical Procedure for the Conversion of 7 into 10 To a solution of amino alcohol 7 (150 mg, 0.73 mmol) in MeOH-H2O (2:1, 3 mL) at r.t. were added CuSO4·5H2O (18 mg, 0.073 mmol, 1 M solution in H2O) and K2CO3 (101 mg, 0.73 mmol, followed by slow addition of Nf-N3 (475 mg, 1.46 mmol) via syringe. The mixture was stirred for 24 h, then glycine hydrochloride (554 mg, 5 mmol) was added in order to quench the reaction mixture and the suspension was stirred for another 24 h. The mixture was filtered and the solvents were removed. The crude solid was dissolved in pyridine (6 mL) and cooled to 0°C. Then DMAP (3 mg, 0.02 mmol) and Ac2O (0.69 mL, 7.3 mmol) were added and the mixture was stirred at r.t. for 12 h. The residue was taken up in Et2O and washed with a 1 M solution of HCl and brine followed by a sat. solution of NaHCO3. The organic layer was dried MgSO
    • +: 314.1349; found: 314.1352.
  • 27
    • 34548148681 scopus 로고    scopus 로고
    • Typical Procedure for the Conversion of 10 into 14 To a solution of azide 10 (15 mg, 42 μmol) and phenyl acetylene 12 (5.0 μL, 42 μmol) in MeCN (0.78 mL) were added solutions of Et3N (840 μL, 8.4 μmol, 10 mM solution in MeCN, TBTA (8.4 μmol, 840 μL of a 10 mM solution in MeCN, and CuI (8.4 μmol, 840 μL of a 10 mM solution in MeCN, Argon was bubbled through the mixture for 15 min and the reaction was stirred for 24 h at 40°C. Then H2O (5 mL) and EtOAc (5 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 3 mL, The combined organic layers were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, hexane-EtOAc, 6:4 to pure EtOAc) to give 14 (18 mg, 90% yield) as a colorless solid. Analytical Data for 3S,4S,5R,6S, Acetic A
    • +: 460.2078; found: 460.2091.
  • 30
    • 31144455167 scopus 로고    scopus 로고
    • For examples of triazole-linked pseudo-oligosaccharides, see: (a) Hotha, S, Kashyap, S. J. Org. Chem. 2006, 71, 364
    • For examples of triazole-linked pseudo-oligosaccharides, see: (a) Hotha, S.; Kashyap, S. J. Org. Chem. 2006, 71, 364.
  • 32
    • 34548152289 scopus 로고    scopus 로고
    • These compounds are currently being tested as selectin binding substrates in collaboration with J. Dernedde, R. Tauber, Charité- Universitätsmedizin Berlin, CBF, Zentralinstitut für Laboratoriumsmedizin und Pathobiochemie
    • These compounds are currently being tested as selectin binding substrates in collaboration with J. Dernedde, R. Tauber, Charité- Universitätsmedizin Berlin, CBF, Zentralinstitut für Laboratoriumsmedizin und Pathobiochemie.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.