Syntheses of deoxyhexoses from diastereoisomerically pure hetero-Diels-Alder adduct

✍ Scribed by Tomasz Bauer

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 269 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00159-2

✦ Synopsis

Syntheses of deoxyhexoses are presented. The concept is based on the functionalization of enantiomerically pure 6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran, which is easily synthesized by asymmetric hetero-Diels-Alder reaction. Methyl 4,6-dideoxy-a-o-arabino-hexopyranoside, methyl a-o-chalcoside and methyl c~-D-desosanimide are synthesized.