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Volumn 39, Issue 28, 1998, Pages 4937-4940

Preparation of a fluorous benzyl protecting group and its use in a fluorous synthesis approach to a disaccharide

Author keywords

[No Author keywords available]

Indexed keywords

ACETONYLACETONE; BENZYL DERIVATIVE; DISACCHARIDE; FLUORINE DERIVATIVE; GALACTOSE; GLUCONATE CALCIUM; OLIGOSACCHARIDE;

EID: 0032500101     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00961-7     Document Type: Article
Times cited : (120)

References (26)
  • 5
    • 0028116495 scopus 로고
    • 2. a) Introduction to "fluorous biphasic catalysis", Horvath, I. T.; Rabai, J. Science 1994, 266, 72.
    • (1994) Science , vol.266 , pp. 72
    • Horvath, I.T.1    Rabai, J.2
  • 6
    • 0030772233 scopus 로고    scopus 로고
    • b) Overview of recent progress in "fluorous biphasic catalysis": Cornils, B. Angew. Chem. Int. Ed. Eng. 1997, 36, 2057.
    • (1997) Angew. Chem. Int. Ed. Eng. , vol.36 , pp. 2057
    • Cornils, B.1
  • 9
    • 0031098534 scopus 로고    scopus 로고
    • 4. a) Some of these features are shared by polyethylene glycol (PEG) tagging methods. Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. For a related strategy based on lipophilic tagging, see
    • (1997) Chem. Rev. , vol.97 , pp. 489
    • Gravert, D.J.1    Janda, K.D.2
  • 14
    • 0010441113 scopus 로고    scopus 로고
    • note
    • 14, mostly perfluorohexane.
  • 20
    • 0000974143 scopus 로고    scopus 로고
    • 3, which is sold inexpensively under the name Oxsol-2000™ by Oxychem. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
    • (1997) J. Org. Chem. , vol.62 , pp. 450
    • Ogawa, A.1    Curran, D.P.2
  • 23
    • 0032565080 scopus 로고    scopus 로고
    • 12. Extraction experiments showed that galactose 6 does not partition into FC-72, so this impurity cannot originate from residual 6 from the coupling which was not removed by extraction. Even chromatographically purified samples of the fluorous disaccharides provided 6, suggesting that this is formed during the hydrogenation step. Further support for this came from a control hydrogenation with the standard (non-fluorous) tribenzyl disaccharide, which provide small amounts of diacetone galactose and 2-deoxyglucose (isolated as their peracetate derivatives). See: Urbanek, R. A.; Salaes, S. F.; Forsyth, C.. J. Am. Chem. Soc. 1998, 120, 2523.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2523
    • Urbanek, R.A.1    Salaes, S.F.2    Forsyth, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.