Method for azide displacement of .alpha.-triflates of 1,5-lacton

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536119, 549283, 549285, C07H 1302, C07D31102

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active

050215620

ABSTRACT:
Reactions of azide ion with 2-O-trifluoromethanesulphonates of both 3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heltono-1,5-lactone and of 3,4:6,7-di-O-isopropylidene-D-glycero-D-galactoheptono-1,5-lactone are disclosed to give predominantly 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-galacto-heptono-1, 5-lactone initially which then isomerizes under moderate reaction conditions to 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1, 5-lactone.

REFERENCES:
Fleet, Tetrahedron 45, 319-326, (1989).
Bashyal et al., Tetrahedron 43, 415-422 (1987).
Bashyal et al., Tetrahedron 43, 423-430 (1987).
Montgomery and Hudson, J. Am. Chem. Soc. 64, 247 (1942).
Karabinos et al., J. Am. Chem. Soc. 75, 4320 (1953).
Baird et al., J. Chem. Soc. Perkin Trans. 1, 1785-1791 (1987).
Dho et al., Tetrahedron Lett. 27, 3203-3204 (1986).
Nash et al., Tetrahedron 44, 5959-5964 (1988).
Kite et al., Tetrahedron Lett. 29, 6483-6486 (1988).
Fleet et al., Ibid. 25, 4029-4032 (1984).
Fleet et al., Tetrahedron 43, 979-990 (1987).

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