Integrated route to the L-aldohexoses using a common man-made chiral building block

✍ Scribed by Miwako Takeuchi; Takahiko Taniguchi; Kunio Ogasawara

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 178 KB
• Volume: 12
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(2000)12:5/6<338::aid-chir6>3.0.co;2-y

✦ Synopsis

Starting from a common man-made chiral sugar building block, five out of eight L-aldohexoses have been synthesized in a diastereocontrolled manner to complete an integrated synthesis of the eight possible aldohexoses; the remaining three L-hexoses were synthesized from the same building block. Thus, L-altrose, L-mannose, L-allose, L-talose, and L-glucose were obtained in the present investigation on the basis of the inherent convex-face selectivity exerted by the chiral building block.