Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-09-06
1976-06-01
Brown, Johnnie R.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
424180, C07H 506, C07H 1522
Patent
active
039608379
ABSTRACT:
O-2,6-Diamino-2,3,4,6-tetradeoxy-.alpha.-D-erythro-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 known as aminotrideoxybutirosin A, and acid-addition salts. They have a wide spectrum of antibacterial activity.
The above compounds can be produced from aminodeoxybutirosin A by the sequence of reactions which comprises protecting the five primary amino groups by converting them to arylmethoxycarbonyl derivatives, converting the 3',4'-hydroxyl groups to an acetal, acylating the remaining four hydroxyl groups, and hydrolyzing the acetal to produce a key intermediate which is an O-2,6-dideoxy-2,6-bis[[(arylmethoxy)carbonyl]amino]-.alpha.-D-glucopyranos yl-(1.fwdarw.4)-O-[2,3-di-O-acyl-5-deoxy-5-[[(arylmethoxy)carbonyl]amino]-. beta.-D-xylofuranosyl-(1.fwdarw.5)]-6-O-acyl-N.sup.1 -[(S)-2-acyloxy-1-oxo-4-[[(arylmethoxy)carbonyl]amino]-butyl]-2-deoxy-N.su p.3 -[(arylmethoxy)carbonyl]streptamine, generically also identified as protected 5"-aminodeoxybutirosin A. That compound is reacted with methanesulfonyl chloride in pyridine to introduce 3',4'-methanesulfonyloxy groups which are removed by reaction with zinc and sodium iodide to introduce a double bond at the 3',4' position. The acyl groups are hydrolyzed or cleaved as by reaction with ammonia in methanol and the product is reacted with hydrogen in the presence of a catalyst to remove the arylmethoxycarbonyl groups and hydrogenate the double bond with the formation of aminotrideoxybutirosin A.
REFERENCES:
patent: 3541078 (1970-11-01), Woo et al.
patent: 3753973 (1973-08-01), Umezawa et al.
patent: 3784541 (1974-01-01), Culbertson et al.
Ellis, "Hydrogenation of Organic Substances" Van Nostrand Co., 1930, p. 197.
Wagner and Zook, "Syn. Org. Chemistry" Wiley and Sons, Inc., 1953, p. 171.
Brown Johnnie R.
Owens Cary
Parke, Davis & Company
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