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Volumn , Issue 13, 2006, Pages 2075-2078

Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides

Author keywords

Glycosylations; L biopterin glycosides; Limipterin; Protecting groups; Pteridine

Indexed keywords

2' O ACETYL N 2 (N,N DIMETHYLAMINOMETHYLENE) 1' O (4 METHOXYBENZYL) 3 [2 (4 NITROPHENYL)ETHYL] BIOPTERIN; BIOPTERIN; UNCLASSIFIED DRUG;

EID: 33748286171     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949620     Document Type: Article
Times cited : (15)

References (41)
  • 9
    • 0002551482 scopus 로고
    • Blakley, R.; Benkovic, S. J., Eds.; J. Wiley and Sons: New York
    • (b) Kaufman, S.; Kaufman, E. E. In Folates and Pterins, Vol. 2; Blakley, R.; Benkovic, S. J., Eds.; J. Wiley and Sons: New York, 1985, 251-352.
    • (1985) Folates and Pterins , vol.2 , pp. 251-352
    • Kaufman, S.1    Kaufman, E.E.2
  • 31
    • 84950215313 scopus 로고
    • Addition of 2,2-dimethoxypropane gave a higher yield of 6 (80%) than that of reported method by use of only acetone (68%): Gigg, R.; Payne, S.; Conant, R. J. Carbohydr. Res. 1983, 2, 207.
    • (1983) J. Carbohydr. Res. , vol.2 , pp. 207
    • Gigg, R.1    Payne, S.2    Conant, R.3
  • 32
    • 33748256740 scopus 로고    scopus 로고
    • note
    • When acidic hydrolysis of methyl 2,3-O-isopropylidene-4-O-PMB-α-L- rhamnopyranoside was attempted to obtain 4-O-PMB-L-rhamnose(8), removal of the PMB group preferentially took place rather than hydrolysis of methyl glycoside. Therefore we employed 1-propenyl glycoside, which is cleavable under weaker acidic conditions.
  • 34
    • 33748256168 scopus 로고
    • US 3505329, 1970
    • Weinstock, J. US 3505329, 1970; Chem. Abstr. 1970, 72, 132787h.
    • (1970) Chem. Abstr. , vol.72
    • Weinstock, J.1
  • 35
    • 33748255337 scopus 로고    scopus 로고
    • note
    • A similar condensation of non-protected 5-deoxy-L-erythro-pentos-2-ulose with the same pyrimidine derivative has been reported to provide an 8:2 mixture of 6- and 7-substituted pterins in a relatively low yield (37%; ref. 18).
  • 36
    • 33748283616 scopus 로고    scopus 로고
    • note
    • 3): δ = 15.61 (C-3′), 71.94 (C-2′), 82.26 (C-1′), 129.29 (C-4a), 159.98 (C-7), 140.92 (C-6), 153.17 (C-8a), 157.88 (C-2), 161.83 (C-4).
  • 39
    • 33748260057 scopus 로고    scopus 로고
    • note
    • 4 as an activator resulted in the formation of diol 4 by cleavage of PMB group instead of glycosylation.
  • 41
    • 33748255579 scopus 로고    scopus 로고
    • note
    • 4), and evaporated in vacuo. The residue was purified by column chromatography to give the 2′-O-glucopyranosyl-L- biopterin derivative.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.