Synthesis of 1,2-dioxetanes
US4956477A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 22, 1989 |
| Grant date | Sep 11, 1990 |
| Priority date | — |
| Expiry date | Sep 22, 2009 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2603/74
- WIPO fieldMeasurement
- WIPO sectorInstruments
Abstract
Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## 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 ##STR5## are produced by reacting a compound of the formula ##STR6## 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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.