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Volumn 54, Issue 10, 1998, Pages 2059-2074

A detailed investigation of the preparation of 2,7-diaminosuberic acid and 2,5-diaminoadipic acid derivatives using Kolbe electrolysis

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIAMINOADIPIC ACID; 2,7 DIAMINOSUBERIC ACID; ACID; UNCLASSIFIED DRUG;

EID: 0032485445     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10412-4     Document Type: Article
Times cited : (42)

References (32)
  • 12
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    • c) Schäfer, H.-J. Angew. Chem. 1981, 93, 978-1000; Angew. Chem. Int. Ed. Engl. 1981, 20, 911.
    • (1981) Angew. Chem. , vol.93 , pp. 978-1000
    • Schäfer, H.-J.1
  • 13
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    • c) Schäfer, H.-J. Angew. Chem. 1981, 93, 978-1000; Angew. Chem. Int. Ed. Engl. 1981, 20, 911.
    • (1981) Angew. Chem. Int. Ed. Engl. , vol.20 , pp. 911
  • 17
    • 0010580050 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 93 24,523
    • b) Undheim, K.; Kremminger, P. PCT Int. Appl. WO 93 24,523; Chem. Abstracts 1995, 122, 10682a.
    • Undheim, K.1    Kremminger, P.2
  • 18
    • 3743115370 scopus 로고
    • b) Undheim, K.; Kremminger, P. PCT Int. Appl. WO 93 24,523; Chem. Abstracts 1995, 122, 10682a.
    • (1995) Chem. Abstracts , vol.122
  • 19
    • 0010618614 scopus 로고    scopus 로고
    • note
    • 14 Di-Boc-L,L-DAS-di-OH (12) was obtained in 18% yield with the Kolbe electrolysis and with 20% yield using the procedure described in ref. 13a. trans-1,4-Dibromo-2-butene was used for the dialkylation step because of higher diastereoselectivity compared to cis 1,4-dibromo-2-butene, 1,4-dibromobutane or 1,4-dibromo-2-butyne. The isolated yield of the dialkylation product was 45% because repeated crystallization was necessary to reach a diastereoselectivity >95%.
  • 21
    • 0010579657 scopus 로고    scopus 로고
    • as replacement for cystine: see ref. 1; ref. 2; ref. 9
    • 16 a) as replacement for cystine: see ref. 1; ref. 2; ref. 9;
  • 22
    • 0030970263 scopus 로고    scopus 로고
    • b) as replacement for bis-(homocysteine) to stabilize a helical conformation: Andrews, M. J. I.; Tabor, A. B. Tetrahedron Lett. 1997, 38, 3063-3066.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3063-3066
    • Andrews, M.J.I.1    Tabor, A.B.2
  • 23
    • 0010580359 scopus 로고    scopus 로고
    • c) as precursors for the preparation of rigid dipeptide mimetics: (i) Mueller, R.; Revesz, L. Tetrahedron Lett. 1997, 38, 3063-3066. (ii) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437-9446 and references therein.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3063-3066
    • Mueller, R.1    Revesz, L.2
  • 24
    • 0030446803 scopus 로고    scopus 로고
    • and references therein
    • c) as precursors for the preparation of rigid dipeptide mimetics: (i) Mueller, R.; Revesz, L. Tetrahedron Lett. 1997, 38, 3063-3066. (ii) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437-9446 and references therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 9437-9446
    • Lombart, H.-G.1    Lubell, W.D.2
  • 27
    • 0010611181 scopus 로고    scopus 로고
    • note
    • 19 We also investigated the Kolbe electroysis of Fmoc-Glu-OtBu. Unfortunately, no desired product of di-Fmoc-DAS-di-OtBu could be isolated from the reaction mixture.
  • 29
    • 0010616742 scopus 로고    scopus 로고
    • Unfortunately, Boc-Asp-OMe is not commercially available at the moment
    • 21 Unfortunately, Boc-Asp-OMe is not commercially available at the moment.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.