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Volumn 58, Issue 44, 2002, Pages 9049-9054

Synthesis of 3-deoxy-2-ulosonic acid KDO and 4-epi-KDN, a highly efficient approach of 3-C homologation by propargylation and oxidation

Author keywords

Carbohydrates; KDN; KDO; Oxidation; Propargylation; Ulosonic acid

Indexed keywords

2,3:5,6 DI O ISOPROPYLIDENE MANNITOL; 3 DEOXY 2 ULOSONIC ACID; 3 DEOXY MANNO OCTULOSONIC ACID; 4 EPI 3 DEOXY GLYCEROGALACTO 2 ULOSONIC ACID; ALKYNE; FUNCTIONAL GROUP; FURAN DERIVATIVE; GLUCONO ALPHA LACTONE ALDEHYDE; PYRUVIC ACID; SUGAR ACID; UNCLASSIFIED DRUG;

EID: 0037191036     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01129-8     Document Type: Article
Times cited : (28)

References (12)
  • 1
    • 0001643728 scopus 로고
    • (a) Levin D.H., Racker E. J. Biol. Chem. 234:1959;2532-2539 (b) Unger F.M. Adv. Carbohydr. Chem. Biochem. 38:1981;323-388.
    • (1959) J. Biol. Chem. , vol.234 , pp. 2532-2539
    • Levin, D.H.1    Racker, E.2
  • 5
    • 0035208486 scopus 로고    scopus 로고
    • and a listing of earlier approaches cited therein
    • For chemical syntheses of KDO and related compounds, see: (a) Sugisaki C.H., Ruland Y., Clezio I.L., Baltas M. Synlett. 2001;1905-1908 (b) Sarabia F., Lopez-Herrera F.J. Tetrahedron Lett. 42:2001;8801-8804 (c) Kumaran G., Mootoo D.R. Tetrahedron Lett. 42:2001;3783-3785 (d) Reiner M., Schmidt R.R. Tetrahedron: Asymmetry. 11:2000;319-335 (e) Mlynarski J., Banaszek A. Org. Lett. 1:1999;1709-1711 (f) Burke S.D., Sametz G.M. Org. Lett. 1:1999;71-74 (g) Bräuer N., Kirschning A., Schaumann E. Eur. J. Org. Chem. 1998;2729-2732 (h) Mikshiev Y.M., Paidak B.B., Kornilev V.I., Zhdanov Y.A. Russ. J. Gen. Chem. 68:1998;1168-1169 (i) Schlessinger R.H., Pettus L.H. J. Org. Chem. 63:1998;9089-9094 (j) Jiang S., Rycroft A.D., Singh G., Wang X.-Z., Wu Y.-L. Tetrahedron Lett. 39:1998;3809-3812 (k) Hu Y.-J., Huang X.-D., Yao Z.-J., Wu Y.-L. J. Org. Chem. 63:1998;2456-2461 (l) Schmidt R.R., Betz R. Angew. Chem., Int. Ed. Engl. 23:1984;430-431 (m) Danishefsky S.J., Pearson W.H., Segmuller B.E. J. Am. Chem. Soc. 107:1985;1280-1285 (n) López-Herrera F.J., Sarabia-Garcia F. Tetrahedron. 53:1997;3325-3346 (o) Tsukamoto H., Takahashi T. Tetrohedron Lett. 38:1997;6415-6418 (p) Miynarski J., Banaszek A. Tetrahedron: Asymmetry. 11:2000;3737-3746 (q) Kumaran G., Mootoo D.R. Tetrahedron Lett. 42:2001;3783-3785 (r) Gao J., Härter R., Gordon D.M., Whitesides G.M. J. Org. Chem. 59:1994;3714-3715. and a listing of earlier approaches cited therein. For enzymatic syntheses of KDO and related compounds, see: (s) Kragl U., Gödde A., Wandrey C., Lubin N., Augé C. J. Chem. Soc., Perkin Trans. 1. 1994;119-124 (t) Sugai T., Shen G.-J., Ichikawa Y., Wong C.-H. J. Am. Chem. Soc. 115:1993;413-421 (u) Augé C., Bouxom B., Cavayé B., Gautheron C. Tetrahedron Lett. 30:1989;2217-2220 (v) Bednarski M.D., Crans D.C., DiCosimo R., Simon E.S., Stein P.D., Whitesides G.M., Schneider M.J. Tetrahedron Lett. 29:1988;427-430.
    • (2001) Synlett , vol.42 , pp. 1905-1908
    • Sugisaki, C.H.1    Ruland, Y.2    Clezio, I.L.3    Baltas, M.4
  • 6
    • 0026710275 scopus 로고
    • (a) Wu W.-L., Wu Y.-L. Tetrahedron Lett. 33:1992;3887-3890 (b) Wu W.-L., Wu Y.-L. J. Chem. Soc., Perkin Trans. 1. 1992;2705-2707 (c) Wu W.-L., Wu Y.-L. J. Chem. Soc., Chem. Commun. 1993;821-822 (d) Wu W.-L., Wu Y.-L. J. Chem. Soc., Perkin Trans. 1. 1993;3081-3086 (e) Wu W.-L., Yao Z.-J., Li Y.-L., Li J.-C., Xia Y., Wu Y.-L. J. Org. Chem. 60:1995;3257-3259.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3887-3890
    • Wu, W.-L.1    Wu, Y.-L.2
  • 12
    • 85077634689 scopus 로고
    • (a) Mitsunobu O. Synthesis. 1981;1-28 (b) Brussani G., Ley S.V., Wright J.L., Williams D.J. J. Chem. Soc., Perkin Trans. 1. 1986;303-307.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1


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