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Volumn 64, Issue 42, 2008, Pages 9928-9936

Stereoselective synthesis of azetidine-derived glutamate and aspartate analogues from chiral azetidin-3-ones

Author keywords

[No Author keywords available]

Indexed keywords

(1 TOSYLAZETIDINE 2,3 DIYL)DIMETHANOL; 1 BENZYL 2 (HYDROXYMETHYL)AZETIDINE 3 CARBONITRILE; 1 BENZYL 2 [(TERT BUTYLDIPHENYLSILYLOXY)METHYL]AZETIDINE 3 CARBONITRILE; 2 ((TERT BUTYLDIPHENYLSILYOXY)METHYL) 1 TOSYLAZETIDIN 3 YL)METHANOL; 2 [(TERT BUTYLDIPHENYLSILYOXY)METHY] 3 METHYLENE 1 TOSYLAZETIDINE; 2 PHENYL 1 TOSYL 3 VINYLAZETIDINE; 2 PHENYL 1 TOSYLAZETIDIN 3 ONE; 3 (CARBOXYMETHYL) 1 TOSYLAZETIDINE 2 CARBOXYLIC ACID; 3 (CARBOXYMETHYL)AZETIDINE 2 CARBOXYLIC ACID; 6 TOSYL 3 OXA 6 AZABICYCLO[3.2.0]HEPTAN 2 ONE; ASPARTIC ACID; AZETIDIN 3 ONE DERIVATIVE; AZETIDINE; AZETIDINE 2,3 DICARBOXYLIC ACID; AZETIDINE DERIVATIVE; ETHYL 2 (2 PHENYL 1 TOSYLAZETIDIN 3 YL)ACETATE; ETHYL 2 (2 PHENYL 1 TOSYLAZETIDIN 3 YLIDENE)ACETATE; GLUTAMIC ACID DERIVATIVE; METHYL 3 (2 ETHOXY 2 OXOETHYL) 1 TOSYLAZETIDINE 2 CARBOXYLIC ACID; METHYL 3 [(METHOXYCARBONYL)METHYL] 1 TOSYLAZETIDINE 2 CARBOXYLIC ACID; N (3 DIAZO 2 OXO 1 PHENYLPROPYL) 4 METHYLBENZENESULFONAMIDE; N TOSYL 2 PHENYLGLYCINE; RHODIUM; TERT BUTYL 2 [(TERT BUTYLDIPHENYLSILYOXY) METHYL] 3 HYDROXYAZETIDINE 1 CARBOXYLIC ACID; TERT BUTYL 2 [(TERT BUTYLDIPHENYLSILYOXY)METHYL] 3 (METHYLSULFONYLOXY)AZETIDINE 1 CARBOXYLIC ACID; TERT BUTYL 2 [(TERT BUTYLDIPHENYLSILYOXY)METHYL] 3HYDROXYAZETIDINE 1 CARBOXYLIC ACID; TOLUENE; UNCLASSIFIED DRUG;

EID: 50549094193     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.001     Document Type: Article
Times cited : (16)

References (56)
  • 14
    • 0002837109 scopus 로고
    • Conformationally Constrained Amino Acids as Probes of Glutamate Receptors and Transporters
    • Kozikowski A.P. (Ed), Raven, New York, NY
    • Chamberlin A.R., and Bridges R.J. Conformationally Constrained Amino Acids as Probes of Glutamate Receptors and Transporters. In: Kozikowski A.P. (Ed). Drug Design for Neuroscience (1993), Raven, New York, NY 231-259
    • (1993) Drug Design for Neuroscience , pp. 231-259
    • Chamberlin, A.R.1    Bridges, R.J.2
  • 34
    • 0002523213 scopus 로고
    • Compound 4 was also prepared by Pusino:
    • Compound 4 was also prepared by Pusino:. Pusino A., Saba A., and Desole G. Gazz. Chim. Ital. 115 (1985) 33
    • (1985) Gazz. Chim. Ital. , vol.115 , pp. 33
    • Pusino, A.1    Saba, A.2    Desole, G.3
  • 36
    • 50549095397 scopus 로고    scopus 로고
    • For previous applications of the Wittig olefination of azetidin-3-ones, see:
    • For previous applications of the Wittig olefination of azetidin-3-ones, see:
  • 41
    • 50549091394 scopus 로고    scopus 로고
    • note
    • The cis compound 6 could not be separated from its trans isomer by column chromatography.
  • 43
    • 50549099667 scopus 로고    scopus 로고
    • note
    • The use of diazomethane was merely to facilitate isolation and purification of 9. Compound 9 was obtained as an inseparable mixture of the cis and trans stereoisomers.
  • 47
    • 50549093160 scopus 로고    scopus 로고
    • note
    • In some occasions, a small amount of epimerization at C2 was observed.
  • 48
    • 50549094187 scopus 로고    scopus 로고
    • note
    • Attempts to carry out this epimerization step beyond the cis/trans ratio of 20:80 were fruitless. As a typical procedure, 0.10 mmol of compound 12 is dissolved in 3.0 mL of dry toluene. After that, 10 equiv of pure DBU is added and the solution stirred under reflux for 7 h. After cooling, the solution is filtered in a short pad of silica and the silica washed with 30% EtOAc/hexanes. The organic layers are combined and evaporated to yield the epimerized trans diester in 60% yield as a inseparable mixture of isomers (8:2 trans:cis).
  • 54
    • 50549094323 scopus 로고    scopus 로고
    • note
    • Conditions employed different protocols for Jones oxidation and IBX oxidation to the aldehyde, followed by Pinick oxidation.
  • 56
    • 50549097802 scopus 로고    scopus 로고
    • note
    • Frank Lovering Ph.D. Thesis (www.umi.com/proquest), under the supervision of Richard Chamberlin (University of California, Irvine).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.