title: Efficient, diastereoselective chemical synthesis of a beta-mannopyranosyl phosphoisoprenoid.
abstract: [reaction: see text] Tetrabutylammonium benzyl dihydrophytylphosphate was coupled to S-phenyl 2,3-di-O-benyl-4, 6-O-benzylidene-1-thio-alpha-D-mannopyranoside S-oxide on activation with triflic anhydride in toluene at -78 degrees C to give the corresponding beta-mannosyl phosphate in 56% yield with no detectable formation of the alpha-anomer. Treatment with sodium in liquid ammonia then afforded the unprotected beta-mannosyl phosphoisoprenoid.
authors: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
authors: D
authors: D
authors: Crich
authors: V
authors: V
authors: Dudkin
mesh_terms: D002473:Cell Wall / Q000737:chemistry; D009162:Mycobacterium avium / Q000737:chemistry*; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D011103:Polyisoprenyl Phosphate Monosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011103:Polyisoprenyl Phosphate Monosaccharides