Glycosylation of exo-glycals

Details Glycosylation of exo-glycals Glycosylation of exo-glycals

2006-07-18

2006-07-18

Jiang, Shaojia A. (Department: 1623)

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

Organic compounds

Carbohydrates or derivatives

C536S123100, C536S001110, C568S959000

Reexamination Certificate

active

07078520

ABSTRACT:
This invention relates to a method of preparing a first alicyclic compound having a vinyl group on one alkyl ring carbon and an alkoxy, cycloalkoxy, heterocycloalkyoxy, aryloxy, or heteroaryloxy group on the same ring carbon; the method comprising reacting an aliphatic alcohol or an aromatic alcohol with a second alicyclic compound having an exo cyclic carbon-carbon double bond, wherein the non-ring olefinic carbon is substituted with a hydroxymethyl, thiomethyl, alkoxymethyl, aryloxymethyl, acyloxymethyl, alkylsulfonyloxymethyl, arylsulfonyloxymethyl, alkylsulfonylmethyl, arylsulfonylmethyl, halomethyl, or silyloxymethyl group.

REFERENCES:
Lin, H-C, Organic Letters, 2003, 5(&), 1087-1089.
Chang et al., “Inter- and Intramolecular Alcohol Additions to Exo-glycals”, Tetrahedron Letters 43:6515-6519, 2002.
Lin et al., “Steroselective Glycosylation of Exo-Glycals Accelerated by Ferrier-Type Rearrangment”, Organic Letters 5:1087-1089, 2003.
Yang et al., “Expeditious Synthesis of C-Glycosyl Conjugated Dienes and Aldehydes from Sugar Lactones”, Tetrahedron Letters 42:4657-4660, 2001.
Yang et al., “Facile Synthesis of Conjugated Exo-glycals”, Tetrahedron Letters 42:6907-6910, 2001.
Yang et al., “Stereochemistry in the Synthesis and Reaction of Exo-glycals”, J. Org. Chem., 67:3773-3782, 2002.

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