Integrated route to the L-aldohexoses using a common man-made chiral building block.
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.
Takeuchi
M
M
Pharmaceutical Institute, Tohoku University, Aobayama, Sendai, Japan.
Taniguchi
T
T
Ogasawara
K
K
D002621:Chemistry / Q000379:methods; D005947:Glucose / Q000737:chemistry; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry; D008956:Models, Chemical; D013237:Stereoisomerism
D006601:Hexoses; C002055:allose; D005947:Glucose; D008358:Mannose