{"search_session":{},"preferences":{"l":"en","queryLanguage":"en"},"patentId":"US_7652172_B2","frontPageModel":{"patentViewModel":{"ref":{"entityRefType":"PATENT","entityRefId":"041-375-159-955-860"},"entityMetadata":{"linkedIds":{"empty":true},"tags":[],"collections":[{"id":8756,"type":"PATENT","title":"Princeton University Patent Portfolio","description":"","access":"OPEN_ACCESS","displayAvatar":true,"attested":false,"itemCount":5503,"tags":[],"user":{"id":91044780,"username":"Cambialens","firstName":"","lastName":"","created":"2015-05-04T00:55:26.000Z","displayName":"Cambialens","preferences":"{\"usage\":\"public\",\"beta\":false}","accountType":"PERSONAL","isOauthOnly":false},"notes":[{"id":8201,"type":"COLLECTION","user":{"id":91044780,"username":"Cambialens","firstName":"","lastName":"","created":"2015-05-04T00:55:26.000Z","displayName":"Cambialens","preferences":"{\"usage\":\"public\",\"beta\":false}","accountType":"PERSONAL","isOauthOnly":false},"text":"
Search applicants and owners = \"Princeton University\", \" University Princeton\", \"Princeton Univ\", \"Univ Princeton\", \" Princet* Univ*\", \"Trustees Univ* Princet*\".
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Total patents= 4986
Search applicants and owners = \"Princeton University\", \" University Princeton\", \"Princeton Univ\", \"Univ Princeton\", \" Princet* Univ*\", \"Trustees Univ* Princet*\".
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Total patents= 4986
a) reacting gluconic acid γ-lactone with dimethoxycyclohexanone for a time and under conditions to produce 5,6-O-cyclohexylidene-glucono-1,4-lactone;\n
b) subjecting said lactone to oxidative cleavage to produce 2,3-O-cyclohexylidene-glyceraldehyde;\n
c) halogenating said glyceraldehyde under conditions to produce 1,1-dihalo-3,4-cyclohexylidenedioxybut-1-ene (“dihaloalkene”);\n
d) purifying said dihaloalkene and further reacting said dihaloalkene under conditions to convert the alkene moiety of said dihaloalkene to an alkyne anion;\n
e) quenching said anion with either\n\ni) a methylating agent to produce 1,1-dihalo-3,4-cyclohexylidenedioxypent-3-yne, or\nii) water to produce 1,1-dibromo-3,4-cyclohexylidenedioxybut-3-yne, followed by methylation to produce 1,1-dibromo-3,4-cyclohexylidenedioxypent-3-yne, and recovering said alkyne;\n
f) oxidizing said alkyne in non-aqueous solution under conditions to produce 4,5-cyclohexylidenedioxy-2,3-pentadione, which is said protected DPD; and\n
g) recovering said protected DPD."],"number":1,"annotation":false,"title":false,"claim":true},{"lines":["The method of claim 1, wherein said gluconic acid γ-lactone is a racemic mixture of the L- and D-stereoisomers of gluconic acid γ-lactone and said protected DPD is a racemic mixture of (S)-4,5-cyclohexylidenedioxy-2,3-pentadione and (R)-4,5-cyclohexylidenedioxy-2,3-pentadione."],"number":2,"annotation":false,"title":false,"claim":true},{"lines":["A method to stereospecifically synthesize protected DPD which comprises\n
a) reacting the desired stereoisomer of gluconic acid γ-lactone with dimethoxycyclohexanone for a time and under conditions to produce 5,6-O-cyclohexylidene-glucono-1,4-lactone;\n
b) subjecting said lactone to oxidative cleavage to produce 2,3-O-cyclohexylidene-glyceraldehyde;\n
c) halogenating said glyceraldehyde under conditions to produce 1,1-dihalo-3,4-cyclohexylidenedioxybut-1-ene (“dihaloalkene”);\n
d) purifying said dihaloalkene and further reacting said dihaloalkene under conditions to convert the alkene moiety of said dihaloalkene to an alkyne anion;\n
e) quenching said anion with either\n\ni) a methylating agent to produce 1,1-dihalo-3,4-cyclohexylidenedioxypent-3-yne, or\nii) water to produce 1,1-dibromo-3,4-cyclohexylidenedioxybut-3-yne, followed by methylation to produce 1,1-dibromo-3,4-cyclohexylidenedioxypent-3-yne, and recovering said alkyne;\n
f) oxidizing said alkyne in non-aqueous solution under conditions to produce 4,5-cyclohexylidenedioxy-2,3-pentadione, which is said protected DPD; and\n
g) recovering said protected DPD having the desired stereospecificity."],"number":3,"annotation":false,"title":false,"claim":true},{"lines":["The method of claim 1, wherein said gluconic acid γ-lactone is L-gluconic acid γ-lactone and said protected DPD is (S)-4,5-cyclohexylidenedioxy-2,3-pentadione."],"number":4,"annotation":false,"title":false,"claim":true},{"lines":["The method of claim 1, wherein said gluconic acid y-lactone is D-gluconic acid γ-lactone and said protected DPD is (R)-4,5-cyclohexylidenedioxy-2,3-pentadione."],"number":5,"annotation":false,"title":false,"claim":true},{"lines":["The method of claim 1 or 3, wherein isotopically labelled compounds are produced by using a methylating agent with an isotope of carbon-12 in step e)."],"number":6,"annotation":false,"title":false,"claim":true},{"lines":["The method of claim 6, wherein the isotope is 13C or 14C."],"number":7,"annotation":false,"title":false,"claim":true},{"lines":["A method to synthesize protected DPD which comprises\n
a) preparing an 5,6-O-alkylidene-protected gluconic acid γ-lactone having a protecting group represented by the formula\n\nwherein R is independently alkyl having from 3 to 8 carbon atoms, aryl, or when taken together, form a cycloalkyl ring having from 4 to 8 carbon atoms;\n
b) subjecting said lactone to oxidative cleavage to produce 2,3-O-alkyldeneglyceraldehyde;\n
c) halogenating said glyceraldehyde under conditions to produce a 1,1-dihalo-3,4-alkylidenedioxybut-1-ene (“dihaloalkene”);\n
d) purifying said dihaloalkene and further reacting said dihaloalkene under conditions to convert the alkene moiety of said dihaloalkene to an alkyne anion;\n
e) quenching said anion with either\n\ni) a methylating agent to produce 1,1-dihalo-3,4-alkylidenedioxypent-3-yne, or\nii) water to produce 1,1-dibromo-3,4-alkylidenedioxybut-3-yne, followed by methylation to produce 1,1-dibromo-3,4-alkylidenedioxypent-3-yne, and recovering said alkyne;\n
f) oxidizing said alkyne in non-aqueous solution under conditions to produce 4,5-alkylidenedioxy-2,3-pentadione, which is said protected DPD; and\n
g) recovering said protected DPD."],"number":8,"annotation":false,"title":false,"claim":true}]}},"filters":{"npl":[],"notNpl":[],"applicant":[],"notApplicant":[],"inventor":[],"notInventor":[],"owner":[],"notOwner":[],"tags":[],"dates":[],"types":[],"notTypes":[],"j":[],"notJ":[],"fj":[],"notFj":[],"classIpcr":[],"notClassIpcr":[],"classNat":[],"notClassNat":[],"classCpc":[],"notClassCpc":[],"so":[],"notSo":[],"sat":[]},"sequenceFilters":{"s":"SEQIDNO","d":"ASCENDING","p":0,"n":10,"sp":[],"si":[],"len":[],"t":[],"loc":[]}}