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Volumn 7, Issue 13, 2005, Pages 2591-2594

Effective synthesis of 1β-acyl glucuronides by selective acylation

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; GLUCURONIDE; MORPHOLINE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM;

EID: 29844439969     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0507165     Document Type: Article
Times cited : (45)

References (32)
  • 13
    • 0000287232 scopus 로고
    • The original report of the use of the Mitsunobu procedure for glycosyl ester synthesis was by: Smith, A. B.; Hale, K. J.; Rivero, R. A. Tetrahedron Lett. 1986, 27, 5813-5816.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5813-5816
    • Smith, A.B.1    Hale, K.J.2    Rivero, R.A.3
  • 16
    • 0037155542 scopus 로고    scopus 로고
    • Recent investigations have shown that, for some hindered secondary alcohols, the Mitsunobu reaction may proceed via an acyloxyphosphonium intermediate: Ahn, C.; Correia, R.; De Shong, P. J. Org. Chem. 2002, 67, 1751-1753.
    • (2002) J. Org. Chem. , vol.67 , pp. 1751-1753
    • Ahn, C.1    Correia, R.2    De Shong, P.3
  • 17
    • 0000870705 scopus 로고    scopus 로고
    • Scheme 2 posits the "normal" alkoxyphosphonium intermediate; we consider the anomeric position is not particularly hindered. See also: Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967-2971.
    • (1996) J. Org. Chem. , vol.61 , pp. 2967-2971
    • Hughes, D.L.1    Reamer, R.A.2
  • 20
    • 29844436199 scopus 로고    scopus 로고
    • note
    • Available from Sigma-Aldrich Co. Glucuronic acid in DMF was stirred with allyl bromide (1.1 equiv) and the resin-bound base at 40°C for 16 h followed by filtration, evaporation and chromatography.
  • 27
    • 29844453087 scopus 로고    scopus 로고
    • note
    • Covalent binding of the deprotected product to monophosphate dehydrogenase has been demonstrated, with superior response to enzymatically prepared material. Further details will be published elsewhere.
  • 31
    • 29844458720 scopus 로고    scopus 로고
    • note
    • 2, silica) then afforded the free acyl glucuronide, e.g., 16a.
  • 32
    • 29844447947 scopus 로고    scopus 로고
    • note
    • 11 as a foam (0.108 g, 52%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.