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Volumn , Issue 10, 1999, Pages 2623-2632

Synthesis of verbascoside: A dihydroxyphenylethyl glycoside with diverse bioactivity

Author keywords

Caffeic acid; Carbohydrates; Glycosidations; Orthoester

Indexed keywords

ACTEOSIDE; GLYCOSIDE;

EID: 0032869837     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k     Document Type: Article
Times cited : (65)

References (46)
  • 1
    • 0028312287 scopus 로고
    • and references cited therein
    • [1a] For a review on the distribution of phenylethyl glycosides in the plant kingdom and their biological activity see: C. Jiménez, R. Riguera, Nat. Prod. Rep. 1994, 11, 591-606 and references cited therein. For other interesting bioactivities of verbascoside, see:
    • (1994) Nat. Prod. Rep. , vol.11 , pp. 591-606
    • Jiménez, C.1    Riguera, R.2
  • 12
    • 0344965444 scopus 로고    scopus 로고
    • note
    • [6a] It has been reported
  • 13
    • 0344103051 scopus 로고    scopus 로고
    • note
    • that ethyl 1-thiorhamnopyranosides are more reactive than the corresponding mannopyranosides.
  • 16
    • 0344534399 scopus 로고    scopus 로고
    • note
    • [17b] Prepared in the same way as 3a
  • 17
    • 0344103050 scopus 로고    scopus 로고
    • note
    • starting from 1,2,3,4-O-tetrabenzoyl-αβ-L-rhamnose.
  • 18
    • 0344534398 scopus 로고    scopus 로고
    • note
    • 2THF.
  • 22
    • 0344965441 scopus 로고    scopus 로고
    • note
    • The negative outcome of the glycosidation may be explained by the occurrence of a competing electrophilic aromatic substitution of the electron-rich phenyl ring in 12.
  • 24
    • 0344534395 scopus 로고    scopus 로고
    • note
    • [13a] Interestingly, no reaction of 6a with NIS in the presence of acetic acid [9] in dichloromethane was observed, indicating that 6a is more "disarmed" [13b] than a fully benzoylated ethyl 1-thiopyranosyl donor.
  • 26
    • 0344965439 scopus 로고    scopus 로고
    • note
    • 2) was accompanied by cleavage of the benzylidene acetal.
  • 29
    • 0344534394 scopus 로고    scopus 로고
    • note
    • Monitoring the coupling reaction of 8a with 12 by TLC analysis revealed the presence of an intermediate, which was tentatively assigned as the corresponding orthoester.
  • 35
    • 0030998721 scopus 로고    scopus 로고
    • To prevent migration of the caffeoyl ester function from HO-4 to HO-6 under mild basic conditions, the primary hydroxy group was protected with an acid-labile dimethoxytrityl (DMT) group see: S-Q. Zhang, Z-J. Li, A-B. Wang, M-S. Cai, R. Feng, Carbohvdr. Res. 1997, 299, 281-285.
    • (1997) Carbohvdr. Res. , vol.299 , pp. 281-285
    • Zhang, S.-Q.1    Li, Z.-J.2    Wang, A.-B.3    Cai, M.-S.4    Feng, R.5
  • 39
    • 0001001018 scopus 로고
    • [26a] Cleavage of the phenolic silyl protecting groups with TBAF was reported to be troublesome; see: P. M. Kendall, J. V. Johnson, C. E. Cook, J. Org. Chem. 1979, 44, 1421-1424. See for alternative desilylation of phenolic tert-butyldimethylsilyl ethers:
    • (1979) J. Org. Chem. , vol.44 , pp. 1421-1424
    • Kendall, P.M.1    Johnson, J.V.2    Cook, C.E.3
  • 42
    • 0030053285 scopus 로고    scopus 로고
    • and references cited therein
    • [26d] N. S. Wilson, B. A. Keay, Tetrahedron Lett. 1996, 37, 153-156 and references cited therein.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 153-156
    • Wilson, N.S.1    Keay, B.A.2
  • 44
    • 0029841253 scopus 로고    scopus 로고
    • [26f] For an excellent review on selective deprotection of silyl ethers, see: T. D. Nelson, R. D. Crouch, Synthesis 1996, 1031-1069.
    • (1996) Synthesis , pp. 1031-1069
    • Nelson, T.D.1    Crouch, R.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.