Methyl 4-O-(trichloroacetamidoyl)-2, 3, 6-trideoxy-α-L-threo-hex-2-enopyranoside (6), prepared from methyl 2, 3, 6-trideoxy-α-L-threo-hex-2-enopyranoside (5), was cyclized to the iodooxazoline 7 which, by hydrolysis under acidic conditions, afforded the corresponding hydrochloride 8. The deiodination reaction was performed with Bu3SnH and methyl 3-amino-2, 3, 6-trideoxy-α-L-lyxopyranoside hydrochloride (methyl α-L-daunosaminide hydrochloride) 1 was obtained in 80% yield. The intermediate 5 was synthesizedstarting from methyl 4-O-mesyl-2, 3, 6-trideoxy-α-L-erythro-hex-2-enopyranoside 3 in 80% yield by means of carbonate anion on polymeric support. © 1984, American Chemical Society. All rights reserved.
Cardillo G., Orena M., Sandri S., Tomasini C. (1984). Regio- and Stereoselective Synthesis of Methyl α-L-Daunosaminide Hydrochloride. JOURNAL OF ORGANIC CHEMISTRY, 49(21), 3951-3953 [10.1021/jo00195a013].
Regio- and Stereoselective Synthesis of Methyl α-L-Daunosaminide Hydrochloride
Orena M.Data Curation
;Tomasini C.Investigation
1984
Abstract
Methyl 4-O-(trichloroacetamidoyl)-2, 3, 6-trideoxy-α-L-threo-hex-2-enopyranoside (6), prepared from methyl 2, 3, 6-trideoxy-α-L-threo-hex-2-enopyranoside (5), was cyclized to the iodooxazoline 7 which, by hydrolysis under acidic conditions, afforded the corresponding hydrochloride 8. The deiodination reaction was performed with Bu3SnH and methyl 3-amino-2, 3, 6-trideoxy-α-L-lyxopyranoside hydrochloride (methyl α-L-daunosaminide hydrochloride) 1 was obtained in 80% yield. The intermediate 5 was synthesizedstarting from methyl 4-O-mesyl-2, 3, 6-trideoxy-α-L-erythro-hex-2-enopyranoside 3 in 80% yield by means of carbonate anion on polymeric support. © 1984, American Chemical Society. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
