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.

Regio- and Stereoselective Synthesis of Methyl α-L-Daunosaminide Hydrochloride / Cardillo G.; Orena M.; Sandri S.; Tomasini C.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 49:21(1984), pp. 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.
1984
Regio- and Stereoselective Synthesis of Methyl α-L-Daunosaminide Hydrochloride / Cardillo G.; Orena M.; Sandri S.; Tomasini C.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 49:21(1984), pp. 3951-3953. [10.1021/jo00195a013]
Cardillo G.; Orena M.; Sandri S.; Tomasini C.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/914574
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