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Synthesis of 3-Acetamido-3-deoxy-(1→5)-α-D-ribofuranan by Ring-Opening Polymerization of 1,4-Anhydro-3-azido-α-D-ribopyranose Derivative

1999; Springer Nature; Volume: 31; Issue: 2 Linguagem: Inglês

10.1295/polymj.31.167

1349-0540

Gereltu Borjihan, Kohsaku Okuyama, Kaname Katsuraya, Toshiyuki Uryu,

Carbohydrate Chemistry and Synthesis

A stereoregular 3-acetamido-3-deoxy-(1→5)-α-D-ribofuranan (3AAdRF) was synthesized by the synthetic route starting from selective ring-opening polymerization of 1,4-anhydro-3-azido-2-O-t-butyldimethylsilyl-3-deoxy-α-D-ribopyranose (A3ASR). A3ASR was polymerized by BF3·OEt2 catalyst at low temperature to give 3-azido-2-O-t-butyl-dimethylsilyl-(1→5)-α-D-ribofuranan (3AzSRF) with M̄n of 1.4×104—1.9×104 and [α]D of +249—+266°. 3AzSRF was reduced with NaBH4 in a tetrahydrofuran (THF)–ethanol mixture to afford 3-amino-2-O-t-butyldimethylsilyl-3-deoxy-(1→5)-α-D-ribofuranan (3AmSRF). Acetylation of the amino group in 3AmSRF produced 3-acetamido-ribofuranan derivative (3AAdSRF), and then desilylation of the 3AAdSRF gave 3AAdRF with M̄n ranging from 9.4×103 to 10.5×103 and [α]d of +195°. The structure analysis was performed by 13C and 1H NMR spectroscopy, IR spectroscopy, and optical rotation measurements.