Synthesis of 1,2-dioxetanes and intermediates therefor

Details Synthesis of 1,2-dioxetanes and intermediates therefor Synthesis of 1,2-dioxetanes and intermediates therefor

C - Chemistry, Metallurgy

07

D

260/446.1, 204/9

C07D 321/00 (2006.01) C07C 43/178 (2006.01) C07C 43/196 (2006.01) C07C 43/215 (2006.01) C07C 69/00 (2006.01) C07F 9/12 (2006.01) C07F 9/655 (2006.01) C07F 9/6574 (2006.01) C07H 15/203 (2006.01) C07H 15/26 (2006.01) C12Q 1/34 (2006.01) G01N 21/76 (2006.01) G01N 33/58 (2006.01)

Patent

CA 1341210

Compounds having the formula: (see formula I) wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: (see formula II) with an R-ylating agent (e.g., R2 SO4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: (see formula III) are produced by reacting a compound having the formula: (see formula IV) with (see formula V) wherein X is an electronegative leaving group (e. g., a halogen anion such as chloride ion) in the presence of a Lewis base (e. g., a trialkyl-amine) dissolved in an aprotic organic solvent (e. g., benzene or toluene). Also, compounds having the formula (see formula VI) are produced by reacting a compound of the formula (see formula VII) with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups. The aforementioned compounds and procedures are useful in the synthesis of enzyme-cleavable 1,2-dioxetane ring systems that can serve as members of a binding pair employed, for example, in chemiluminescent immunoassays, DNA probe assays, and direct assays for an enzyme.

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