Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Sugar moiety of antitumor antibiotic bleomycin

Tetrahedron

Volumn 53, Issue 32, 1997, Pages 10993-11006

  Oshitari, Tetsuta ^a   Shibasaki, Masakatsu ^a   Yoshizawa, Takeshi ^b   Tomita, Masahiro ^b   Takao, Ken Ichi ^c   Kobayashi, Susumu ^c  

^a UNIVERSITY OF TOKYO   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^c TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BLEOMYCIN DERIVATIVE; DISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; DRUG SYNTHESIS; GLYCOSYLATION; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030798036     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00360-8     Document Type: Article

References (34)

1. (a) Umezawa, H.; Maeda, K.; Takita, T.; Okami, Y. J. Antibiot. Ser.A 1966, 19, 200-209.
2. Umezawa, H. Lloydia 1977, 40, 67-81.
3. (a) Sugiura, Y.; Takita, T.; Umezawa, H. In "Metal Ions in Biological Systems" Sigel, H., Ed.; Marcel Dekker: New York, 1985; pp81-108.
4. (b) Hecht, S. M. Acc. Chem. Res. 1986, 19, 383-391.
5. Stubbe, J ; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136.
6. Takita, T.; Muraoka, Y.; Nakatani, T.; Fujii, A.; Umezawa, Y.; Naganawa, H.; Umezawa, H. J. Antibiot. 1978, 31, 801-804.
7. Ohno, M.; Otsuka, M. In "Recent Progress in the Chemical Synthesis of Antibiotics" Lukacs, G.; Ohno, M. Ed.; Springer-Verlag: New York, 1990; pp387-414.
8. Suga, A.; Sugiyama, T.; Otsuka, M.; Ohno, M.; Sugiura, Y.; Maeda, K. Tetrahedron 1991, 47, 1191-1204, and references cited therein.
9. Owa, T.; Haupt, A.; Otsuka, M.; Kobayashi, S.; Tomioka, N.; Itai, A.; Ohno, M.; Shiraki, T.; Uesugi, M.; Sugiura, Y.; Maeda, K. Tetrahedron 1992, 48, 1193-1208, and references cited therein.
10. (a) Kono, A.; Kojima, M.; Maeda, T. Japanese Journal of Clinical Radiology 1973, 18, 195-196.
11. (b) Maeda, T. ibid. 1973, 18, 197-200.
12. (a) Sugiura, Y.; Suzuki, T.; Otsuka, M.; Kobayashi, S.; Ohno, M.; Takita, T.; Umezawa, H. J. Biol. Chem. 1983, 258, 1328-1336.
13. (b) Otsuka, M.; Nishio, T.; Oshitari, T.; Owa, T.; Sugiura, Y.; Maeda, K.; Ohno, M.; Kobayashi, S. Heterocycles 1992, 33, 27-34.
14. Oshitari, T.; Tomita, M.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 6493-6494.
15. Oshitari, T.; Kobayashi, S. Tetrahedron Lett. 1995, 36, 1089-1092.
16. Takita, T.; Umezawa, Y.; Saito, S.; Morishima, H.; Naganawa, H.; Umezawa, H.; Tsuchiya, T.; Miyake, T.; Kageyama, S.; Umezawa, S.; Muraoka, Y.; Suzuki, M.; Otsuka, M.; Narita, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1982, 23, 521-524.
17. (a) Aoyagi, Y.; Katano, K.; Suguna, H.; Primeau, J.; Chang, L.-H.; Hecht, S. M. J. Am. Chem. Soc. 1982, 104, 5537-5538.
18. (b) Katano, K.; Chang, P.-I.; Millar, A.; Pozsgay, V.; Minster, D. K.; Ohgi, T.; Hecht, S. M. J. Org. Chem. 1985, 50, 5807-5815.
19. Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647-5656.
20. (a) Boger, D. L.; Colletti, S. L.; Honda, T.; Menezes, R. F. J. Am. Chem. Soc. 1994, 116, 5607-5618.
21. (b) Boger, D. L.; Honda, T.; Dang, Q. ibid. 1994, 116, 5619-5630.
22. Boger, D. L.; Honda, T.; Menezes, R, F.; Colletti, S. L. ibid. 1994, 116, 5631-5646.
23. Numberings are expressed according to those of L-gulose or D-mannose in this paper.
24. 12
25. Pougny, J.-R.; Nassr, M. A. M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1981, 375-376.
26. Mitsunobu, O. Synthesis 1981, 1-28.
27. Kruizinga, W. H.; Strijtveen, B.; Kellogg, R. M. J. Org. Chem. 1981, 46, 4321-4323.
28. Corey, E. J.; Nicolaou, K. C.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1975, 658-659.
29. RajanBabu, T. V.; Fukunaga, T.; Reddy, G. S. J. Am. Chem. Soc. 1989, 111, 1759-1769.
30. Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159-7161.
31. Nagashima, N.; Ohno, M. Chem. Lett. 1987, 141-144.
32. Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021-3028.
33. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1983, 24, 4037-4040.
34. Schmidt, R. R.; Michel, J. Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.