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Volumn 7, Issue 4, 2005, Pages 745-748

De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYGLUCOSE; GALACTOSE; LACTONE DERIVATIVE; OSMIUM;

EID: 14844356105     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050044i     Document Type: Article
Times cited : (77)

References (28)
  • 3
    • 1642407159 scopus 로고    scopus 로고
    • Fraser-Reid, B. O., Tatsuta, K., Thiem, J., Eds.; Springer: Berlin, Germany
    • (c) Vogel, P. In Glycoscience; Fraser-Reid, B. O., Tatsuta, K., Thiem, J., Eds.; Springer: Berlin, Germany, 2001; Vol. 2, pp 1023-1174.
    • (2001) Glycoscience , vol.2 , pp. 1023-1174
    • Vogel, P.1
  • 5
    • 0000460802 scopus 로고    scopus 로고
    • For related work published since 1996, see ref 5
    • For a review of other approaches to hexoses, see: Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195-1220. For related work published since 1996, see ref 5.
    • (1996) Chem. Rev. , vol.96 , pp. 1195-1220
    • Hudlicky, T.1    Entwistle, D.A.2    Pitzer, K.K.3    Thorpe, A.J.4
  • 14
    • 0037318117 scopus 로고    scopus 로고
    • Although it is a rare sugar, L-galacto-1,4-lactone is a naturally occurring metabolite produced in plants as an intermediate in the biosynthesis of vitamin C, see: Smirnoff, N. Nat. Biotechnol. 2003, 21, 134-136.
    • (2003) Nat. Biotechnol. , vol.21 , pp. 134-136
    • Smirnoff, N.1
  • 15
    • 0345869117 scopus 로고    scopus 로고
    • It has been suggested that the level of the important antioxidant ascorbic acid can be increased by treatment with L-galacto-1,4-lactone, see: Smirnoff, N. Philos. Trans. R. Soc. London 2001, 335, 1455-1464.
    • (2001) Philos. Trans. R. Soc. London , vol.335 , pp. 1455-1464
    • Smirnoff, N.1
  • 27
    • 14844354558 scopus 로고    scopus 로고
    • note
    • This decrease in substrate control can be seen in that when 8a/b were exposed to the achiral UpJohn conditions approximately 1:1 mixtures of 9a/b to 11a/b were formed.
  • 28
    • 14844341140 scopus 로고    scopus 로고
    • note
    • 2PHAL and not an enantiomer, the diastereomeric ratios for the conversion of 8a/b to 9a/b should be slightly different than the ratio for the conversion of 8a/b to 11a/b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.