Synthesis of 1,2-dioxetanes and intermediates therefor
1. Field of the Invention Compounds having the formula: wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a Calkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g.,m-phenylene), produced by reacting a compound having the formula: with an R-ylating agent (...
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| Main Authors | , |
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| Format | Patent |
| Language | English |
| Published |
09.07.2002
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| Online Access | Get full text |
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| Summary: | 1. Field of the Invention
Compounds having the formula: wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a Calkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g.,m-phenylene), produced by reacting a compound having the formula: with an R-ylating agent (e.g., RSO) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: are produced by reacting a compound having the formula: with 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 are produced by reacting a compound of the formula 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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