Synthesis of solanum glycosides

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C536S005000, C536S006100, C536S018500, C536S018600

Reexamination Certificate

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07435816

ABSTRACT:
The present invention relates to the chemical synthesis of solanum glycosides, in particular to the synthesis of solasonine as well as to novel β-monosaccharide intermediate compounds, of Formula (2), where R1is a benzylidene, 4-nitrobenzylidene or 4-methoxybenzylidine group, and each R2independently is a benzoyl, acetyl or pivaloyl group:

REFERENCES:
patent: 6242583 (2001-06-01), Schmidt et al.
patent: WO 03/018604 (2003-03-01), None
Awad, L.F., et al., “A Synthesis of 3-O-(α-D-Mannopyranosyl)-D-Mannose and Its Protein Conjugate,”Carbohydrate Research 122:69-79, 1983.
Fewell, A.M., et al., “Interactions Between the Glycoalkaloids Solasonine and Solamargine in Relation to Inhibition of Fungal Growth,”Phytochemistry 37(4):1007-1011, 1994.
Figueroa-Pérez, S., and V. Vérez-Bencomo, Synthesis of a Sialyl-α-(2→6)-Lactosamine Trisaccharide With a 5-Amino-3-Oxapentyl Spacer Group at C-1I,Carbohydrate Research 317:29-38, 1999.
Fürstner, A., et al., “Ring-Closing Alkyne Metathesis. Application to the Total Synthesis of Sophorolipid Lactone,”J. Org. Chem. 65:8758-8762, 2000.
Li, B., et al., “An Improved Synthesis of the Saponin, Polyphyllin D,”Carbohydrate Research 331:1-7, 2001.
Sugiyama, S., and J.M. Diakur, “A Convenient Preparation of Glycosyl Chlorides From Aryl/Alkyl Thioglycosides,”Organic Letters 2(17):2713-2715, 2000.

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