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Volumn 60, Issue 35, 2004, Pages 7579-7589

First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle

Author keywords

Amino acids; Chiral pool; Natural products; Nitrogen heterocycles; Total synthesis

Indexed keywords

ANTIINFECTIVE AGENT; CARBONYL DERIVATIVE; FLUOROPHOSPHATE; HETEROCYCLIC COMPOUND; HOMOARGININE; N,N DIMETHYLACETAMIDE; O (7 AZABENZOTRIAZOL 1 YL) N,N,N',N' TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE; PYRIMIDINONE DERIVATIVE; TAN 1057 A; UNCLASSIFIED DRUG;

EID: 3843108171     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.034     Document Type: Article
Times cited : (14)

References (29)
  • 4
  • 10
    • 3843060847 scopus 로고    scopus 로고
    • note
    • 5
  • 17
    • 0033986186 scopus 로고    scopus 로고
    • 5-Oxazolidinones from the reaction of hexafluoroacetone and amino acids (simultaneous protection of amino and COOH groups) have already been widely used for the enantioselective synthesis of N-methyl amino acids: (b)
    • 5-Oxazolidinones from the reaction of hexafluoroacetone and amino acids (simultaneous protection of amino and COOH groups) have already been widely used for the enantioselective synthesis of N-methyl amino acids: (b) Burger K., Spengler J. Eur. J. Org. Chem. 2000;199-204
    • (2000) Eur. J. Org. Chem. , pp. 199-204
    • Burger, K.1    Spengler, J.2
  • 18
    • 3843080296 scopus 로고    scopus 로고
    • 11a confirms that the authors of the cited publication also managed to prepare the enatiomerically pure compound
    • 11a confirms that the authors of the cited publication also managed to prepare the enatiomerically pure compound
  • 20
    • 3843137944 scopus 로고    scopus 로고
    • note
    • 20=-42 (c 1.1, MeOH))
  • 21
    • 3843121615 scopus 로고    scopus 로고
    • note
    • An alternative synthesis of the β-amino acid (S)-20a by Wolff-rearrangement of the diazoketone (S)-19 catalyzed by silver benzoate was described in the Supporting Information of Ref. 3
  • 22
    • 3843101103 scopus 로고    scopus 로고
    • 2O). As reported in Ref. 5 the residual amount of MeOH could not be removed even by prolonged drying in high vacuum
    • 2O). As reported in Ref. 5 the residual amount of MeOH could not be removed even by prolonged drying in high vacuum
  • 28
    • 3843151124 scopus 로고    scopus 로고
    • This compound (with an unknown degree of racemization and an unknown optical rotation value) was also found to be an oil: see Supporting Information of Ref. 3
    • This compound (with an unknown degree of racemization and an unknown optical rotation value) was also found to be an oil: see Supporting Information of Ref. 3
  • 29
    • 3843148970 scopus 로고    scopus 로고
    • Data for the monohydrate of the title compound from the Supporting information to Ref. 3. Relative amounts of the solvents are not given
    • Data for the monohydrate of the title compound from the Supporting information to Ref. 3. Relative amounts of the solvents are not given


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.