SYNTHESIS OF 1,2-DIOXETANES AND INTERMEDIATES THEREFOR
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-yl...
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Main Authors | , |
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Format | Patent |
Language | English French |
Published |
27.03.2001
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Edition | 7 |
Subjects | |
Online Access | Get full text |
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Summary: | 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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Bibliography: | Application Number: CA19890587441 |