Synthesis of allofuranose

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

Reexamination Certificate

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Reexamination Certificate

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06858726

ABSTRACT:
The present invention provides a novel strategy for the synthesis of allofuranose using glucofuranose as starting material in a one-pot reaction. The novel finding is that it is possible to carry out the oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose with DMSO/acetic anhydride and a reduction reaction in one pot obtaining high yields of recrystallised and analytical pure 1,2:5,6-di-O-isopropylidene-α-D-allofuranose.

REFERENCES:
patent: 0 379 397 (1990-07-01), None
patent: WO 00 56748 (2000-12-01), None
David C. Baker et al, Carbohydrate Research, 1972, 24, 192-197.*
Sowa, W. et al “The Oxidation of 1,2:5,6-Di-O-Isopropylidene-D-Glucose By Dimethyl Sulfoxide-Acetic Anhydride”, Canadian Journal of Chemistry, 1966, 44, 836-838.*
Fuertes, C. M.,Boletin De La Sociedad Quimica Del Peru, vol. 37, No. 4, 1971, pp. 161-174 [English translation].
Singh, S.K., et al., J.Chem. Commun, pp. 455-456, 1998.
Koshkin, A.A., et al., Tetrahedron, pp. 3607-3630, 1998.
Albright, A.D., e al., Journal of the American Chemical Society, pp. 2416-2423.
Horton, D., et al., Carbohydrate Res. pp. 251-260, 1966.
Horton, D., et al., Carbohydrate Res. pp. 229-232, 1968.
Baker, D.C., et al., Carbohydrate Res. pp. 192-197, 1972.
Sowa, W., et al., Canadian J. Org. Chem. pp. 836-838, 1966.
Youssefyeh, R.D., et al., J. Org. Chem. pp. 1301-1309, 1979.

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