CAS: 26124-68-5; Glycol Acid

专利信息

专利号:US-5756770-A
优先权日:1987-12-31
标题:Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
发明人：BRONSTEIN IRENA Y; EDWARDS BROOKS
权利人:TROPIX INC
摘要:A novel synthesis of 1,2-dioxetane phosphate alkali metal salts and novel intermediates employed in this synthesis are disclosed. A hydroxyaryl enol ether alkali metal salt having the formula: ##STR1## wherein T can be an unsubstituted or substituted adamant-2'-ylidene group, R 3 can be a methyl group, Y can be a phenyl group and M + can be a sodium cation, is reacted with a phosphorohalidate to give the corresponding enol ether ethylene phosphate, which is then reacted with an alkali metal cyanide to give the corresponding enol ether cyanoethyl phosphate diester alkali metal salt intermediate. Singlet oxygen addition to this enol ether cyanoethyl phosphate diester alkali metal salt intermediate to give the corresponding 1,2-dioxetane cyanoethyl phosphate diester alkali metal salt, followed by β-elimination of the cyanoethyl group using an alkali metal hydroxide or the like, gives the corresponding 1,2-dioxetane phosphate alkali metal salt.

专利号:US-2003162992-A1
优先权日:2001-12-14
标 题 :Preparation of intermediates useful in the synthesis of antiviral nucleosides
发明人：WATANABE KYOICHI A; DU JINFA
摘要:The present invention is an efficient process for the manufacture of α-acyloxyacetaldehyde, a key intermediate in the synthesis of 1,3-oxathiolane and 1,3-dioxolane nucleosides.

专利号:EP-0629195-B1
优先权日:1992-03-05
标 题 :Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
发明人：BRONSTEIN IRENA Y; EDWARDS BROOKS
权利人:TROPIX INC
摘要:A novel synthesis of 1,2-dioxetane phosphate alkali metal salts and novel intermediates employed in this synthesis are disclosed. A hydroxyaryl enol ether alkali metal salt having formula (1), wherein T can be an unsubstituted or substituted adamant-2'-ylidene group, R<3> can be a methyl group, Y can be a phenyl group and M<+> can be a sodium cation, is reacted with a phosphorohalidate to give the corresponding enol ether ethylene phosphate, which is then reacted with an alkali metal cyanide to give the corresponding enol ether cyanoethyl phosphate diester alkali metal salt intermediate. Singlet oxygen addition to this enol ether cyanoethyl phosphate diester alkali metal salt intermediate to give the corresponding 1,2-dioxetane cyanoethyl phosphate diester alkali metal salt, followed by beta -elimination of the cyanoethyl group using an alkali metal hydroxide or the like, gives the corresponding 1,2-dioxetane phosphate alkali metal salt.

专利号:WO-9516049-A1
优先权日:1993-12-08
标题 :Catalytic chemo-enzymatic asymmetric synthesis of carbohydrates
发明人：WONG CHI-HUEY; SHARPLESS BARRY K
权利人:SCRIPPS RESEARCH INST; WONG CHI HUEY; SHARPLESS BARRY K
摘要:A stereoselective synthesis of carbohydrates employs two key stereoselective steps, viz. an osmium-catalyzed asymmetric dihydroxylation (AD) of an alkene to form an aldol intermediate and an aldolase-catalyzed aldol addition reaction wherein the aldol intermediate is elongated by the addition of a ketone. Moreover, ketoses having four new stereocenters can be synthesized without the use of chiral starting materials. The stereoselectivity of the asymmetric dihydroxylation (AD) reaction is determined by the cis or trans (Z or E) stereoisomeric configuration of the alkene and by the choice of AD-mix, i.e., an AD-mix-α or AD-mix-β. The stereoselectivity of the aldolase-catalyzed addition reaction is determined by the choice of aldolase and by the stereochemistry of the aldol intermediate. Four aldolases with broad substrate specificity are sufficient to produce all possible enantiomeric combinations of the two hydroxymethylene stereocenters formed during the aldol addition reaction. Accordingly, a synthetic scheme combining an osmium-catalyzed asymmetric dihydroxylation (AD) reaction and an aldolase-catalyzed aldol addition reaction enables direct access to a wide range of carbohydrate derivatives containing up to four new hydroxymethylene stereocenters.

专利号:US-6417380-B1
优先权日:1987-12-31
标 题 :Synthesis of 1,2-dioxetanes and intermediates therefor
发明人：BRONSTEIN IRENA Y; EDWARDS BROOKS
摘要:Compounds having the formula: n wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C 1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., n m-phenylene), produced by reacting a compound having the formula: n with an R-ylating agent (e.g., R 2 SO 4 ) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: n are produced by reacting a compound having the formula: n with n 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 n are produced by reacting a compound of the formula n 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.

专利号:US-5763681-A
优先权日:1989-09-06
标 题 :Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
发明人：EDWARDS BROOKS; JUO RHOU-RONG
权利人:TROPIX INC
摘要:A novel synthesis of compound having the formula: ##STR1## wherein T is a stabilizing spiro-linked polycycloalkylidene group, R 3 is a C 1 -C 20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula: n n (R.sup.1 O).sub.3 P n n wherein R 1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula: n n R.sup.3 OH n n wherein R 3 is as defined above, to produce a 1-alkoxy-1-aryl-methane phosphonate ester of the formula: ##STR2## reacting the phosphonate with base to produce a phosphonate-stabilized carbanion, reacting the carbanion with a ketone of the formula: ##STR3## wherein T is as defined above, to produce an enol ether of the formula: ##STR4## then oxygenating the double bond in the enol ether to give the corresponding 1,2-dioxetane compound.