Synthesis of dibekacin analogs containing 3-oxa- and 3-aza-2,3,4-trideoxy-D-glycero-hexopyranose

Carbohydrate Research

Volumn 293, Issue 1, 1996, Pages 15-30

  Kuwahara, Ryuji ^a   Tsuchiya, Tsutomu ^a  

^a Microbial Chemistry Research Center   (Japan)

Author keywords

5 deoxy 5 fluorination; aminoglycoside antibiotic; glycosylation; Na in liquid NH3; Pb(OAc)4 oxidation; reductive amination

Indexed keywords

DIBEKACIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0030599358     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(96)00176-0     Document Type: Article

References (17)

1. [1] R. Kuwahara and T. Tsuchiya, Carbohydr. Res., 286 (1996) 107-122.
2. [2] S. Umezawa and T. Tsuchiya, J. Antibiot. (Ser. A), 15 (1962) 51-52.
3. [3] T. Jikihara, T. Tsuchiya, S. Umezawa, and H. Umezawa, Bull. Chem. Soc. Jpn., 46 (1973) 3507-3510.
4. [4] T. Tsuchiya, H. Fujita, and S. Umezawa, J. Antibiot. (Ser. A), 17 (1964) 181-185.
5. [5] T. Ogawa, K. Beppu, and S. Nakabayashi, Carbohydr. Res., 93 (1981) C6-C9.
6. [6] Y. Kobayashi and T. Tsuchiya, unpublished data.
7. [7] T. Shitara, E. Umemura, T. Tsuchiya, and T. Matsuno, Carbohydr. Res., 276 (1995) 75-89.
8. [8] Details to be reported elsewhere.
9. [9] G.H. Veeneman, S.H. van Leeuwen, and J.H. van Boom, Tetrahedron Lett., 31 (1990) 1331-1334.
10. [10] Y. Takahashi, T. Tsuchiya, S. Umezawa, and H. Umezawa, Carbohydr. Res., 210 (1991) 221-232.
11. [11] T. Shitara, Y. Kobayashi, T. Tsuchiya, and S. Umezawa, Carbohydr. Res., 232 (1992) 273-290.
12. [12] L. N. Markovskij, V. E. Pashinnik, and A. V. Kirsanov, Synthesis, (1973) 787-789; W. J. Middleton, J. Org. Chem., 40 (1975) 574-578.
13. [12] L. N. Markovskij, V. E. Pashinnik, and A. V. Kirsanov, Synthesis, (1973) 787-789; W. J. Middleton, J. Org. Chem., 40 (1975) 574-578.
14. [13] G. Koyama and Y. Iitaka, Tetrahedron Lett., (1968) 1875-1879.
15. [14] R. F. Borch, M.D. Bernstein, and H. D. Durst, J. Am. Chem. Soc., 93 (1971) 2897-2904.
16. [15] T. Tsuchiya, Y. Takagi, and S. Umezawa, Tetrahedron Lett., (1979) 4951-4954.
17. [16] Details to be reported elsewhere.