Process for the synthesis of 2-deoxy-D-glucose

Details Process for the synthesis of 2-deoxy-D-glucose Process for the synthesis of 2-deoxy-D-glucose

2005-08-23

2005-08-23

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C127S036000

Reexamination Certificate

active

06933382

ABSTRACT:
The present invention provides a process for the synthesis of 2-deoxy-D-glucose comprising haloalkoxylation of R-D-Glucal wherein R is selected from H and 3, 4, 6-tri-O-benzyl, to obtain alkyl 2-deoxy-2-halo-R-α/β-D-gluco/mannopyranoside, converting alkyl 2-deoxy-2-halo-R-α/β-D-gluco/mannopyranoside by reduction to alkyl 2-deoxy-α/β-D-glucopyranoside, hydrolysing alkyl 2-deoxy-α/β-D-glucopyranoside to 2-deoxy-D-glucose.

REFERENCES:
patent: 6319695 (2001-11-01), Wong et al.
Boivin et al., “Synthese D'UN Disaccharide, Constituant Naturel D'Anthracyclines Antibiotiques Et Antitumorales” Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, vol. 21, No. 25, 1980, pp. 2413-2416, (abstract only.
Binkley et al., “Photochemically based Synthesis of Deoxy Sugars, Synthesis of 2-deoxy-D-arabino-hexopyranose (2-deoxy-D-glucose) and several of its derivatives from 3,4,6,-tri-O-acetyl-D-glucal”, Journal of Carbohydrate Chemistry (1982), 1(1), 1-8.
Monneret, et al., “A Convenient Synthesis of 2-deoxy-D-arabino-hexose and of its methyl and benzyl glycosides”, Carbohydrate Research, vol. 96, 1981, pp. 299-305, XP009009800.
Marzabadi et al., “The Chemistry of Glucal Halohydrins: The Effect of the Halide on Epoxide Formation”, Tetrahedron, Elsevier Science Publishers, Amsterdam, NL, vol. 50. No. 23, 1994, pp. 6783-6796, XP001147278.
Kottenhahn et al., “Synthese Von 2-Desoxy-Alpha-O-Glycopeptiden Mit Dem N-Ioduccinimid-(NIS)- Verfahren Synthesis of 2-Deoxy-Alpha-O-Glycopeptides by the N-Iodosuccinimide (NIS) Procedure” Liebigs Annalen der Chemie, Verlag Chemie GMBH, Weinheim, DE, No. 8, 1991, pp. 727-744, XP001147767, (abstract only).
Wëssel et al., “The Synthesis of the 2- and 2′-monodeoxygenated Analogues of Beta-Maltosyl-(1 4) Trehalose” Journal of Carbohydrate Chemistry, New York, NY, US., vol. 17, No. 4/5, May 1998, pp. 567-586, XP009009837.
Costantino et al., “A Mild and Easy One-pot Procedure for the Synthesis of 2-deoxysugars from glycals”, Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, vol. 41, No. 47, Nov. 18, 2000, pp. 9177-9180, XP004236212.
Overend et al., “Deoxy-sugars. Part VII. A Study of the Reactions of Some Derivatives of 2-deoxy-D-glucose”, Journal of the Chemical Society, 1949, pp. 2841-2845.
Friesen, R.W., et al., “On the Controlled Oxidative Coupling of Glycals: A New Strategy for the Rapid Assembly of Oligosaccharides,” J. Am. Chem. Soc., vol. 111, No. 17, 1989, pp. 6656-6660.

Affiliated with

Also associated with

Rating

Process for the synthesis of 2-deoxy-D-glucose does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the synthesis of 2-deoxy-D-glucose, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the synthesis of 2-deoxy-D-glucose will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3474526