Method for producing water-soluble saccharide conjugates and...

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

Reexamination Certificate

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C536S017400, C536S119000, C536S023100, C502S150000, C530S322000, C544S224000, C549S427000, C568S445000, C525S333600, C512S016000, C512S014000

Reexamination Certificate

active

06958395

ABSTRACT:
The present invention relates to a method by which saccharide compounds can be prepared in a very easy way. This method comprises the steps of:(a) attaching at least one saccharide to a cyclic or acyclic diene,(b) reacting the saccharide-containing diene obtained in step (a) or a commercially available saccharide-containing diene with a dienophile by Diels-Alder reaction.

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Jarosz, et al., “Synthesis Of Sugar-Derived 2′-and 3′-Substrituted Furans and Their Application in Diels—Alder Reactions,”Eur. J. Org. Chem.2955-2964 (2001).
Lubineau, et al., “Aqueous Cycloadditions Using Glycoorganic Substrates,”ACS Symposium Series, Chapter 10, pp. 494-156 (1992).
Lubineau, et al., “Preparation of α- and β-dienyl glycosides used as dienes in aqueous Diels-Alder reactions. Influence of the carbohydrated moiety on the thermodynamics of the reaction,”Carbohydrate Research270:163-179 (1995).
Pellegrinet, et al., “Diels-Alder Reactions of D-Glucose-Derived Dienophiles with Cyclophentadiene: A Computational Study,”Tetrahedron56:5311-5316 (2000).
Pontén and Magnusson, “Synthesis of Polycyclic Oxanorbornanes via a Sequential Epoxyhexopyranoside Ring Contraction-Intramolecular Diels-Alder Reaction,”J. Org. Chem.62:7978-7983 (1997).
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