Efficient, diastereoselective chemical synthesis of a beta-mannopyranosyl phosphoisoprenoid.
[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.
Crich
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Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Dudkin
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D002473:Cell Wall / Q000737:chemistry; D009162:Mycobacterium avium / Q000737:chemistry*; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D011103:Polyisoprenyl Phosphate Monosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011103:Polyisoprenyl Phosphate Monosaccharides