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3 (1 equiv) were reacted in toluene in the presence of N-methylmorpholine (2 equiv) for 30 min at 0°C to room temperature. The mixture was filtered under argon to remove the resultant N-methylmorpholine hydrochloride and concentrated to dryness to afford crude 2a-d, which was used without further purification.
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The oxazaphospholidine 6a was synthesized as a mixture of two isomers having either a (2S,4R,5R)- or a (2R,4S,5S)-oxazaphospholidine ring by using racemic 1,2-amino alcohol 7d. The 1,2-amino alcohols 7c,d were synthesized according to the procedures reported in the literature. The details are given in Supporting Information. (a) Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68, 9747-9752.
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The oxazaphospholidine 6a was synthesized as a mixture of two isomers having either a (2S,4R,5R)- or a (2R,4S,5S)-oxazaphospholidine ring by using racemic 1,2-amino alcohol 7d. The 1,2-amino alcohols 7c,d were synthesized according to the procedures reported in the literature. The details are given in Supporting Information. (a) Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68, 9747-9752.
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The nucleoside 3′-O-oxazaphospholidine derivatives 5a-d were partially decomposed on silica gel during chromatography, resulting in modest isolated yields. The isolated 5a-d were stable for at least 1 year under proper storage conditions (at-30°C in a glass vial flushed with an inert gas).
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The nucleoside 3′-O-oxazaphospholidine derivatives 5a-d were partially decomposed on silica gel during chromatography, resulting in modest isolated yields. The isolated 5a-d were stable for at least 1 year under proper storage conditions (at-30°C in a glass vial flushed with an inert gas).
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