Total syntheses of aminomethyl-C-dideoxyglycopyranosides and their quinamides

✍ Scribed by Dmitriy E Gremyachinskiy; Vyacheslav V Samoshin; Paul H Gross

• Book ID: 104254279
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 203 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01692-7

✦ Synopsis

Lewis acid promoted cyclization of homoallylic alcohol 1 with acetal 2 gave 4-chloro-2-phthalimidomethyl-6-methyltetrahydropyrans. Their dehydrochlorination produced two regioisomeric dihydropyrans. Subsequent cis-and trans-dihydroxylation gave four racemic dihydroxy-6-methyl-2-phthalimidomethyl tetrahydropyrans. They were deprotected and N-acylated with a chiral quinic acid lactone, producing a library of four diastereomeric mixtures of novel C-pseudodisaccharides, which were separable after derivatization.