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Volumn , Issue 12, 2009, Pages 1949-1950

Glycotriazolophane synthesis via click chemistry

Author keywords

1,2,3 Triazole; Azide alkyne cycloaddition; Carbohydrates; Cyclophane; Macrocycle

Indexed keywords

ALKYNE; AMINO ACID; CARBOHYDRATE; COPPER; CYCLOPHANE; GLYCOTRIAZOLOPHANE; MACROCYCLIC COMPOUND; SUGAR; TRIAZOLE; UNCLASSIFIED DRUG;

EID: 67651172932     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217534     Document Type: Article
Times cited : (24)

References (34)
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    • For recent reviews on saccharides as polyfunctional scaffolds, see: a
    • For recent reviews on saccharides as polyfunctional scaffolds, see: (a) Velter, I.; La Ferla, B.; Nicotra, F. J. Carbohydr. Chem. 2006, 25, 97.
    • (2006) J. Carbohydr. Chem , vol.25 , pp. 97
    • Velter, I.1    La Ferla, B.2    Nicotra, F.3
  • 14
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    • A triazacyclophane has been investigated in bioactive molecule development, see: a
    • A triazacyclophane has been investigated in bioactive molecule development, see: (a) Opatz, T.; Liskamp, R. M. J. Org. Lett. 2001, 3, 3499.
    • (2001) Org. Lett , vol.3 , pp. 3499
    • Opatz, T.1    Liskamp, R.M.J.2
  • 16
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    • For selected publications on synthesis and applications of glycophanes, see: a
    • For selected publications on synthesis and applications of glycophanes, see: (a) Bukownik, R. R.; Wilcox, C. S. J. Org. Chem. 1988, 53, 463.
    • (1988) J. Org. Chem , vol.53 , pp. 463
    • Bukownik, R.R.1    Wilcox, C.S.2
  • 31
    • 67651198614 scopus 로고    scopus 로고
    • Preparation of 3 and 5 To ice-cold 1 (0.95 g, 2.75 mmol) in CH2Cl2 (anhyd, 20 mL) was added oxalyl chloride (0.25 mL, 3.03 mmol, followed by DMF (0.005 mL) under N2 and the mixture stirred for 0.5 h. p-Xylenediamine (0.169 mg, 1.24 mmol) and DIPEA (0.48 mL, 2.75 mmol) were stirred together in the presence of 4 Å MS in CH 2Cl2 (anhyd, 10 mL) until complete dissolution of the amine. The solution containing the acid chloride was added, and the mixture was stirred for a further 2 h at 0 ° C. The mixture was extracted with CH 2Cl2 (20 mL, washed with NaHCO3 (2 x 15 mL, HCl (2 x 15 mL, brine (2 x 15 mL, H2O (2 x 15 mL, dried (Na 2SO4, filtered, and the solvent removed to give a pale brown foam. Silica gel chromatography (EtOAc-Cy, gradient elution, 1:1 to 2:1) gave the protected diamide as a white foam (0.359 g, 37, This diamide 74
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.