Synthesis of D-glycopyranosyl azides from 1,2-anhydrosugars using lithium azidohydridodiisobutylaluminate

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 543-544

  Lee, Goo Soo ^a   Min, Hye Kyung ^a   Chung, Bong Young ^a  

^a Korea University   (South Korea)

Author keywords

Aluminum and compounds; Azides; Glycosides; Stereoselection

Indexed keywords

AZIDE; GLYCOSIDE; LITHIUM AZIDOHYDRIDODIISOBUTYLALUMINATE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; EPOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033556072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02435-6     Document Type: Article

References (8)

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6. 2(10 ml) and the resulting solution was cooled to 0 °C. A solution of dimethyldioxirane in acetone (0.2 mmol, 0.05-0.1 M) was added dropwise and the reaction mixture was stirred at 0 °C for 1 h. Solvent removal with a stream of dry nitrogen and vacuum drying afforded 1α,2α-anhydro-3,4,6-tri-O-benzyl-D-glucopyranose (2a) in quantitative yield.
7. Lemieux RU, Howard J. 1,2-Anhydro-α-D-glucopyranose triacetate. In: Whistler RL, Wolfrom ML, editors. Methods in Carbohydrate Chemistry , Vol. II. New York: Academic Press, 1963:400-402.
8. D values.