Synthesis of dibekacin (3', 4'-dideoxykanamycin B) from D-glucosamine and D-glucose.

M Yoshikawa, M Torihara, T Nakae, BC Cha…

Index: Yoshikawa; Torihara; Nakae; Cha; Kitagawa Chemical and pharmaceutical bulletin, 1987 ,  vol. 35,  # 5  p. 2136 - 2139

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Citation Number: 4

Abstract

An aminoglycoside antibiotic, dibekacin (= 3', 4'-dideoxykanamycin B)(22), has been synthesized from D-glucosamine and D-glucose using an oxidative decarboxylation reaction with lead tetraacetate and a reductive deacetoxylation reaction with sodium borohydride as keyreactions.

 Related Synthetic Route
(4R,6S,7R,7aS)-7-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-6-(((benzyloxy)carbonyl)amino)-2,2-dimethyl-4-nitrohexahydrobenzo[d][1,3]dioxol-5-yl acetate Structure

113886-52-5

(4R,6S,7R,7aS)-...

~%

diethyl ((1R,3S,4R,5R,6S)-4-(((2R,3R,6S)-6-(acetamidomethyl)-3-((ethoxycarbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)dicarbamate Structure

113922-91-1

diethyl ((1R,3S...

benzyl ((1S,2R,3R,5R)-2-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-3,4,6-trihydroxy-5-nitrocyclohexyl)carbamate Structure

113886-44-5

benzyl ((1S,2R,...

~%

diethyl ((1R,3S,4R,5R,6S)-4-(((2R,3R,6S)-6-(acetamidomethyl)-3-((ethoxycarbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)dicarbamate Structure

113922-91-1

diethyl ((1R,3S...

benzyl ((1S,2R,3R,5R)-2-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-3,4,6-trihydroxy-5-nitrocyclohexyl)carbamate Structure

113886-44-5

benzyl ((1S,2R,...

~%

(4R,6S,7R,7aS)-7-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-6-(((benzyloxy)carbonyl)amino)-2,2-dimethyl-4-nitrohexahydrobenzo[d][1,3]dioxol-5-yl acetate Structure

113886-52-5

(4R,6S,7R,7aS)-...

diethyl ((1R,3S,4R,5R,6S)-4-(((2R,3R,6S)-6-(acetamidomethyl)-3-((ethoxycarbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)dicarbamate Structure

113922-91-1

diethyl ((1R,3S...

(2R,3S,4S,5R,6R)-3,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-bromo-N-(2,4-dinitrophenyl)tetrahydro-2H-pyran-4-amine Structure

113886-46-7

(2R,3S,4S,5R,6R...

~80%

Structure

113886-47-8

(4R,6S,7R,7aS)-7-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-6-(((benzyloxy)carbonyl)amino)-2,2-dimethyl-4-nitrohexahydrobenzo[d][1,3]dioxol-5-yl acetate Structure

113886-52-5

(4R,6S,7R,7aS)-...

~%

Structure

113886-47-8

benzyl ((1S,2R,3R,5R)-2-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-3,4,6-trihydroxy-5-nitrocyclohexyl)carbamate Structure

113886-44-5

benzyl ((1S,2R,...

~%

Structure

113886-47-8

diethyl ((1R,3S,4R,5R,6S)-4-(((2R,3R,6S)-6-(acetamidomethyl)-3-((ethoxycarbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydroxycyclohexane-1,3-diyl)dicarbamate Structure

113922-91-1

diethyl ((1R,3S...

~%

penta-N-acetyldibekacin Structure

108050-24-4

penta-N-acetyld...

(2R,3S,4S,5R,6R)-3,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-bromo-N-(2,4-dinitrophenyl)tetrahydro-2H-pyran-4-amine Structure

113886-46-7

(2R,3S,4S,5R,6R...

~%

penta-N-acetyldibekacin Structure

108050-24-4

penta-N-acetyld...

benzyl ((1S,2R,3R,5R)-2-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-3,4,6-trihydroxy-5-nitrocyclohexyl)carbamate Structure

113886-44-5

benzyl ((1S,2R,...

~%

benzyl ((3aS,4R,5S,7R,7aR)-4-(((2R,3R,6S)-6-(acetamidomethyl)-3-(((benzyloxy)carbonyl)amino)tetrahydro-2H-pyran-2-yl)oxy)-2,2-dimethyl-7-nitrohexahydrobenzo[d][1,3]dioxol-5-yl)carbamate Structure

113886-45-6

benzyl ((3aS,4R...


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