Synthesis of benzyl and methyl 3-benzamido-2,3,6-trideoxy-2-fluoro-β-l-galactopyranoside: Protected C-2 fluoro analogues of daunosamine

Baptistella, Lúcia Helena Brito; Marsaioli, Anita Jocelyne; Filho, José Dias de Souza; Oliveira, Geovane G. de; Oliveira, Alaı́de Braga de; Dessinges, A.; Castillón, Sergio; Olesker, Alain; Thang, Ton That; Lukacs, Gabor

doi:10.1016/0008-6215(85)85048-5

Cited by 17 publications

(13 citation statements)

References 10 publications

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“…The large vicinal coupling constants were indicative of axial protons and consequently of a D-gluco configuration. Interestingly, H-6eq showed up as an octet (^ -ß -ßß* = 9 Hz, 3«/h-6«,,h-5 = 4 Hz, and hJH-e^.F = 2 Hz).…”

Section: Resultsmentioning

confidence: 99%

“…The relatively small geminal couplings 2JC-2,f = 17. 4 Hz and 2JC-4,f = 17.2 Hz were indicative of equatorial substituents on the neighbors of the fluorinebearing carbon. On the other hand, 3JC-i,f = 8.8 Hz revealed a trans relationship between the halogen and the anomeric carbon atom.…”

Section: Resultsmentioning

confidence: 99%

“…To a solution of 3 (4.1 g, 12.1 mmol) in a mixture of 2-methoxyethanol-water (5:1) were added sodium azide (3.4 g, 52.3 mmol) and ammonium chloride (5.6 g, 10.5 mmol) and the mixture was kept at 140 °C overnight. After standard workup, the crude product was chromatographed giving pure 4 (3.7 g, 90%) as a syrup: [apn +88°(c 0.88, chrloroform); mass spectrum, m/z Hz, CH2Ph), 4.32 (ddd, 1 H, J54 = 9 Hz, J6e = 10 Hz, </56, = 5 Hz, H-5), 4.23 (dd, 1 H, Je,5 = 5 Hz, J6-6 = 10 Hz, H-6'), 4.13 (dd, 1 , Ji3 = 4 Hz, </46 9 Hz', H-4), 4.04 '(dd, 1 H, J32 = 3 Hz, J3i = 4 Hz, H-3), 3.93 (br s, 1 , H-2), 3.76 (t, 1 H, J66 = Je6, = 10…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of 2'-C-.beta.-fluorodaunomycin. An example of configurational retention in fluorodehydroxylation with diethylaminosulfur trifluoride

Castillón¹,

Dessinges²,

Faghih³

et al. 1985

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis of 2'-C-.beta.-fluorodaunomycin. An example of configurational retention in fluorodehydroxylation with diethylaminosulfur trifluoride

Castillón¹,

Dessinges²,

Faghih³

et al. 1985

J. Org. Chem.

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“…We now wish to record the coupling of that carbohydrate component with daunomycinone (6), which afforded (S)-2'-fluorodaunorubicin hydrochloride (11). While this work was in progress, various derivatives of 1 were also obtained elsewhere (2)(3)(4)(5), and a coupling reaction with 6 was described ( 3 , similar to ours in principle but different in detail.…”

Section: Introductionmentioning

confidence: 91%

Synthesis and biological activity of (S)-2′-fluorodaunorubicin

Baer¹,

Siemsen²

1988

Can. J. Chem.

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Methyl 3-amino-2,3,6-trideoxy-2-fluoro-~-~-galactopyranoside was hydrolyzed to the free sugar, (S)-2-fluorodaunosamine hydrochloride, which was converted into the a , P -1,4-di-0-acetyl-N-trifluoroacetyl derivative and thence into the corresponding glycosyl bromide. The latter was condensed with daunomycinone, and the product was deprotected to give the title compound. The fluoroanthracycline displayed significant cytotoxicity against a number of tumor cell lines in vitro. Antitumor activity against L1210 murine leukemia in vivo was lower than that of the parent daunorubicin, but toxicity appeared to be reduced. HANS H. BAER et LISA SIEMSEN. Can. J. Chem. 66, 187 (1988).On a hydrolysC l'amino-3 tridtsoxy-2,3,6 fluoro-2 P-L-galactopyrannoside de mCthyle en sucre libre, le chlorhydrate de la fluoro-2-(S) daunosamine, que l'on a transform6 en dtrivt di-0-ac6tyl-a,P-l , 4 N-trifluoroacttyle et finalement en bromure de glycosyle correspondant. On a condense ce demier avec la daunomycinone et on a dtprottgk le produit pour obtenir le composC mentionnt dans le titre. La fluoroanthracycline prtsente une cytotoxicitC in vitro importante contre un certain nombre de lignes de cellules tumorales. L'activitC antitumorale in vivo contre les cellules de murine leuctmique L1210 est plus faible que celle de la daunorubicine parente; toutefois, la toxicit6 semble &tre rtduite.[Traduit par la revue]

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“…The biological properties of the tz,flfluoroamino saccharides (Molloy, Fuller & Hauser, 1973) prompted us to undertake the synthesis of (I) and (II) (Baptistella, Marsaioli, Imamura, Castillon, Olesker & Lukacs, 1985;Baptistella, Marsaioli, Souza Filho et al, 1985) which are fluoro analogues of daunosamine (III) (Horton & Weckerle, 1975), the sugar moiety of the antibiotics daunorubicin and doxorubicin. In the synthesis of (II) we proposed that compound (VI), a key intermediate, could be obtained by treating (IV) (Hanessian & Haskell, 1965) with N-bromosuccinimide followed by AgF/pyridine.…”

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confidence: 99%

Methyl 2,6-anhydro-3-azido-4-O-benzoyl-3-deoxy-α-D-idopyranoside, a new 2,5-dioxabicyclo[2.2.2]octane derivative

Castellano¹,

Oliveira²,

Baptistella³

et al. 1986

Acta Crystallogr C

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Synthesis of benzyl and methyl 3-benzamido-2,3,6-trideoxy-2-fluoro-β-l-galactopyranoside: Protected C-2 fluoro analogues of daunosamine

Cited by 17 publications

References 10 publications

Synthesis of 2'-C-.beta.-fluorodaunomycin. An example of configurational retention in fluorodehydroxylation with diethylaminosulfur trifluoride

Synthesis of 2'-C-.beta.-fluorodaunomycin. An example of configurational retention in fluorodehydroxylation with diethylaminosulfur trifluoride

Synthesis and biological activity of (S)-2′-fluorodaunorubicin

Methyl 2,6-anhydro-3-azido-4-O-benzoyl-3-deoxy-α-D-idopyranoside, a new 2,5-dioxabicyclo[2.2.2]octane derivative

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