New and efficient synthetic routes to 1-deoxy-D-xylulose

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2479-2482

  Giner, José Luis ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYXYLULOSE; 2,3,4 TRIBENZYLTHREITOL; TARTARIC ACID; UNCLASSIFIED DRUG; XYLULOSE;

ANALYTIC METHOD; ARTICLE; BIOSYNTHESIS; CARBOHYDRATE ANALYSIS; HYDROXYLATION; ISOTOPE LABELING; OXIDATION; REACTION ANALYSIS;

EID: 0032559979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00310-4     Document Type: Article

References (25)

1. 1. David, S.; Estramareix, B.; Fischer, J.C.; Therisod, M., J. Am. Chem. Soc. 1981, 103, 7341-7342.
2. 2. Himmeldirk, K.; Kennedy, I.A.; Hill, R.E.; Sayer, B.G.; Spenser, I.D., J. Chem. Soc., Chem. Commun. 1996, 1187-1188.
3. 3. Arigoni, D.; Sagner, S.; Latzel, C.; Eisenreich, W.; Bacher, A.; Zenk, M.H., Proc. Natl. Acad. Sci. USA 1997, 94, 10600-10605.
4. 4. Schwender, J.; Zeidler, J.; Groener, R.; Mueller, C.; Focke, M.; Braun, S.; Lichtenthaler, F.W.; Lichtenthaler, H.K., FEBS Lett. 1997, 414, 129-134.
5. 5. Schwarz, M.K., Ph.D. Thesis Nr. 10951, ETH-Zurich, 1994.
6. 6. Broers, S.T.J., Ph.D. Thesis Nr. 10978, ETH-Zurich, 1994.
7. 7. Rohmer, M.; Seeman, M.; Horbach, S.; Bringer-Meyer, S.; Sahm, H., J. Am. Chem. Soc. 1996, 118, 2564-2566.
8. 8. David, S.; Estramareix, B.; Fischer, J.C.; Therisod, M., J. Chem. Soc., Perkin Trans. 1 1982, 2131-2137.
9. 9. Kennedy, I.A.; Hemscheidt, T.; Britten, J.F.; Spenser, I.D., Can. J. Chem. 1995, 73, 1329-1337.
10. 10. Backstrom, A.D.; Austin, R.; S., M.A.; Begley, T.P., J. Carbohydr. Chem. 1995, 14, 171-175.
11. 2H]-1-deoxy-D-xylulose as its methyl glycoside see ref. 4.
12. +, 2%), 361 (2), 283 (10), 240 (11), 181 (31), 91 (100).
13. +, 1%), 301 (3), 195 (9), 181 (9), 91 (100).
14. 14. Mukai, C.; Moharram, S.M.; Kataoka, O.; Hanaoka, M., J. Chem. Soc., Perkin Trans. 1 1995, 2849-2854.
15. +, 4%), 297 (5), 254 (9), 240 (11), 181 (25), 91 (100).
16. 3): 198.025 (s), 142.873 (d, C-4), 137.639 (s), 130.407 (d, C-3), 128.477 (d, 2C), 127.875 (d), 127.670 (d, 2C), 72.943 (t), 68.822 (t), 27.230 (q).
17. 17. Walsh, P.J.; Sharpless, K.B., Synlett 1993, 605-606.
18. 3): 208.068 (s), 137.599 (s), 128.528 (d, 2C), 127.973 (d), 127.881 (d, 2C), 77.150 (d, C-3), 73.664 (t), 71.013 (t, C-5), 70.459 (d, C-4), 25.565 (q).
19. 19. Gossauer, A.; Suhl, K., Helv. Chim. Acta 1976, 59, 1698-1704.
20. 20. see Giner, J.-L.; Jaun, B.; Arigoni, D., manuscript in preparation.
21. 21. Stipa, P.; Finet, J.P.; Le Moigne, F.; Tordo, P., J. Org. Chem. 1993, 58, 4465-4468.
22. 22. Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230-7237.
23. +, 6%), 145 (40), 117 (15), 107 (24), 105 (15), 91 (100).
24. 24. Shikhiev, I. A.; Karaev, S. F.; Alieva, S. Z.; Yur'eva, G. A. Russ. J. Org. Chem. 1975, 11, 2168-2170.
25. 3): 138.250 (s), 137.084 (d, C-3), 128.369 (d, 2C), 127.733 (d, 2C), 127.611 (d), 126.276 (d, C-4), 72.330 (t), 70.102 (t), 68.212 (d), 23.190 (q).