NEW MATERIAL:A compound shown by the formula I [R is H or tetrahydropyranyl(THP)].
EXAMPLE: 6-C-( 1'-hex-trans-4'-en-1'-ynyl )-5,6-dideoxy-1,2-O-isopropylidene-α-D- xylohexofuranose.
USE: A synthetic intermediate for various organic compounds. Esecially synthetic intermediate for Ceruleniun, an antibiotic, having antifungl and antimicrobial activities.
PROCESS: An ene or yne compound shown by the formula II is reduced in the presence of metal Li, Na, etc. in a mixed solvent of t-butanol, THF, and ammonia, preferably by adding ammonium sulfate to give a debenzylated alcohol compound shown by the formula I. This compound is then reacted with dihydropyragn in the presence of an acid catalyst and converted into a tetrahydropyranyl derivative to give a THP compound shown by the formula I.
Sueda, Noriyoshi
Kuzuhara, Hiromi
Emoto, Sakae
