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DOI: 10.1055/s-2005-917110
Direct Synthesis of Glycidic Bicyclic Scaffolds in Water without Protecting Groups
Publikationsverlauf
Publikationsdatum:
05. Oktober 2005 (online)

Abstract
Bicyclic scaffolds obtained from C-allyl glycosides have been synthesized in water, without the use of protecting groups. The scaffolds have been functionalized with different groups for chemoselective ligation.
Key words
bicyclic scaffold - darbohydrate - green chemistry - unprotected
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References
General Procedure.
Primary alcohol (0.11 mmol) was dissolved in a sat. solution of NaHCO3 (1.5 mL), and then KBr (0.1 equiv) and TEMPO (0.06 equiv) were added. The temperature was lowered to 15-18 °C and an aq solution of NaOCl (5%; 1 mL) was slowly added. The reaction was stirred at r.t. for 2 h then concentrated under reduced pressure. The products were purified by flash chromatography (EtOAc-MeOH-H2O, 6:4:0.5).
Compound 9 (0.15 mmol) and Cs2CO3 (0.15 mmol) were dissolved in dry MeOH (1 mL). After 0.5 h the solution was added to a solution of compound 4a in dry MeOH-DMF 1:1 (2 mL) and left stirring at r.t. for 12 h. The reaction mixture was then concentrated under reduced pressure and the product was purified by flash chromatography (EtOAc-MeOH, 9:1).