From D-xylose to terminal polyols: a simple synthetic route.
A simple and efficient synthetic approach toward different terminal alkyl tetraols and triols, starting from D-xylose, is described. The opening of the oxetane ring in a suitably protected 3,5-anhydro-D-xylose derivative with Grignard reagents leads to D-xylose-derived 5-deoxy-5-C-alkyl derivatives, which are suitable for reduction to terminal polyols after protecting group hydrolysis.
Hadzic
Pavle
P
Institute for Security, Belgrade, Kraljice Ane bb., Serbia. phadzic@yahoo.com
Popsavin
Mirjana
M
D000478:Alkylation; D004988:Ethers, Cyclic / Q000737:chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*; D014994:Xylose / Q000737:chemistry*
D004988:Ethers, Cyclic; D011108:Polymers; C024617:polyol; D014994:Xylose; C005287:oxetane