Process for preparing 5"-amino-4',5"-dideoxybutirosin A

Details Process for preparing 5"-amino-4',5"-dideoxybutirosin A Process for preparing 5"-amino-4',5"-dideoxybutirosin A

1975-04-17

1976-09-28

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

424180, C07H 1522

Patent

active

039831027

ABSTRACT:
O-2,6-diamino-2,4,6-trideoxy-.alpha.-D-xylo-hexopyranosyl-(1.fwdarw.4)-O-[5 -amino-5-deoxy-.beta.-D-xylofuranosyl-(1.fwdarw.5)]-N.sup.1 -[(S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxystreptamine, also named 5"-amino-4',5"-dideoxybutirosin A and acid addition salts of said compounds. These compounds exhibit a wide spectrum of antibacterial activity.
The above compounds can be produced from O-2,6-dideoxy-2,6-bis(Z-amino)-.alpha.-D-glucopyranosyl-(1.fwdarw.4)-O-[2, 3-di-O-acetyl-5-deoxy-5-(Z-amino)-.beta.-D-xylofuranosyl-(1.fwdarw.5)]-6-O- acetyl-N.sup.1 -[(S)-2-acetyloxy-1-oxo-4-(Z-amino)butyl]-2-deoxy-N.sup.3 -streptamine, also named protected 5"-aminodeoxybutirosin A by treating said compound with trifluoromethanesulfonic anhydride and pyridine to yield a mixture containing the 4'-O-(trifluoromethanesulfonyl) compound. The mixture is reacted with the sodium salt of an arylmercaptan and the resulting 4'-arylthio compound is purified and treated with ammonia, thus deprotecting the four hydroxy groups. Lastly, the five amino groups are deprotected and the arylthio group is removed by a reductive cleavage.

REFERENCES:
patent: 3828021 (1974-08-01), Beattle et al.
B371,085, Jan. 1975, Naito et al., 260/210 AB.

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