Two routes to enantiomerically pure 3-aminoinosose derivatives

✍ Scribed by Robert J. Ferrier; Arnold E. Stütz

• Book ID: 102994748
• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 606 KB
• Volume: 200
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(90)84194-y

✦ Synopsis

Epoxidation

with hydrogen peroxide/benzonitrile of (2,!+(2,4/3)-2,3,4-tribcnzyloxycyclohex-5enoneethylene acetal( 13), obtained from methyl 2,3,4-tri-O-benzyl-6-deoxy-a-D-xy[o-hex-5-enopyranoside (9), gave the (2,4/3,5,6)-5,6-anhydride 14 which, with sodium azide in 2-methoxyethanol, gave the (2,4,5/ 3,6)-5-azido-6-hydroxy derivative 15. (2S)-(2,4/3)-2,3,4-Tribenzyloxy-6-phenylsulphonylcyclohex-5-enone ethylene acetal(l8) was also prepared from 13 by reaction in sequence with N-chlorosuccinimide thiophe-201, m-chloroperbenzoic acid, and potassium krt-butoxidc. Treatment of 18 with aqueous ammonia gave the inosamine derivative (2S)-2,4,5/3,6)-5-amino-2,3,4-tribenzyloxy-6-phenylsulphonylcyclohexanone ethylene a&al (20). Compounds 15 and 20 offer a novel access to 3-aminoinosose derivatives and suggest routes to enantiomerically pure compounds such as hydroxyvalidamine, validamine, and inosadiamines related to streptamine and deoxystreptamine.