Chemical immobilization of azido cellulose phenylcarbamate onto silica gel via Staudinger reaction and its application as a chiral stationary phase for HPLC

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5487-5490

  Zhang, Sheng ^a   Ong, Teng Teng ^b   Ng, Siu Choon ^b   On Chan, Hardy Sze ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; AZIDOCELLULOSE PHENYLCARBAMATE; CELLULOSE 6 DEOXY 6 AZIDE PHENYLCARBAMATE; CELLULOSE DERIVATIVE; CHLOROFORM; HEXANE; SILICA GEL; UNCLASSIFIED DRUG; UREA;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATERIAL COATING; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STAUDINGER REACTION;

EID: 34347325034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.167     Document Type: Article

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23. 6) δ: 8.62-8.32 (NH), 7.39-6.75 (arom H), 5.01-3.66 (anhydrous glucose H).
24. 2 was bubbled through the slurry. Cellulose derivative 2 (1.0 g) and triphenylphosphine (1.0 g) were dissolved in THF (100 mL) and added to the reaction mixture, which was stirred at room temperature overnight. The resulting CSP AzCPC-II was filtered and subjected to Soxhlet extraction using THF overnight to remove unreacted 2, after which it was dried under vacuum to afford the desired CSP (yield 3.8 g, 76%). Elemental analysis: C, 10.43; H, 1.69; N, 2.15.
25. Preparation of CSP AzCPC-I: A pre-coating step was performed. Cellulose derivative 2 (1.0 g) was dissolved in THF (20 mL) and coated onto aminized silica (4.2 g). The pre-coated aminized silica gel was dried under vacuum and further chemically bonded under the same conditions described for CSP AzCPC-II except that the solvent was toluene (60 mL) in which 2 was insoluble. The CSP was subjected to the same extraction and drying process to afford the desired CSP (yield 4.0 g, 77%). Elemental analysis: C, 15.58; H, 2.03; N, 3.24.
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