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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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-H2 O, 6:4:0.5).
<A NAME="RG25105ST-9">9 </A>
Compound 9 (0.15 mmol) and Cs2 CO3 (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).