Practical synthesis of 2-keto-3-deoxy-d-glycero-d-galactononulosonic acid (KDN)

Organic Letters

Volumn 13, Issue 23, 2011, Pages 6288-6291

  Crich, David ^a   Navuluri, Chandrasekhar ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEOXYGLYCERO GALACTO NONULOSONIC ACID; 3-DEOXYGLYCERO-GALACTO-NONULOSONIC ACID; SUGAR ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM; SUGAR ACIDS;

EID: 82355182503     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202773t     Document Type: Article

References (19)

1. Angata, T.; Varki, A. Chem. Rev. 2002, 102, 439-469
2. Inoue, S.; Kitajima, K. Glycoconj. J. 2006, 23, 277-290
3. Inoue, S.; Kitajima, K.; Sato, C.; Go, S. Adv. Expt. Med. Biol. 2011, 705, 669-678
4. Crich, D.; Navuluri, C. Angew. Chem., Int. Ed. 2010, 49, 3049-3052
5. Schreiner, E.; Zbiral, E. Liebigs Ann. 1990, 581-586
6. Voight, E. A.; Rein, C.; Burke, S. D. J. Org. Chem. 2002, 67, 8489-8499
7. Banwell, M. G.; Hungerford, N. L.; Jolliffe, K. A. Org. Lett. 2004, 6, 2737-2740
8. Nakamura, M.; Furuhata, K.; Yamasaki, T.; Ogura, H. Chem. Pharm. Bull. 1991, 31, 3140-3144
9. Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228-4232
10. Lin, C. H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138-10145
11. Blixt, O.; Paulson, J. C. Adv. Synth. Catal. 2006, 345, 687-690
12. Gillingham, D. G.; Stallforth, P.; Adibekian, A.; Seeberger, P. H.; Hilvert, D. Nat. Chem. 2010, 2, 102-105
13. Chen, C.; Crich, D. J. Chem. Soc., Chem. Commun. 1991, 1289-1290
14. According to the literature this reaction affords a mixture of isomers favoring the anti -isomer when conducted in diethyl ether: Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 2760-2762
15. van Hooft, P. A. V.; El Oualid, F.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H.; Leeuwenburgh, M. A. Org. Biomol. Chem. 2004, 2, 1395-1403
16. Robertson, J.; Unsworth, W. P.; Lamont, S. G. Tetrahedron 2010, 66, 2363-2372
17. Li, L.-S.; Wu, Y.-L. Tetrahedron 2002, 58, 9049-9054
18. Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758-6763
19. Sheng, L.; Wu, Y.-L. Tetrahedron 2002, 58, 9049-9054