314740-80-2

Upstream product

• 100-51-6 benzyl alcohol 
• 314740-79-9 phosphorous acid benzyl ester 2-cyano-ethyl ester 3,7,11,15-tetramethyl-hexadecyl ester 
• 196197-29-2 O-benzyl-O-β-cyanoethyl-N,N-diisopropylphosphoramidite 
• 7541-49-3 3,7,11,15-tetramethyl-2-hexadecen-1-ol 
• 645-72-7 3,7,11,15-tetramethyl-hexadecanol 

Downstream Products

• 316187-61-8 benzyl 3,7,11,15-tetramethylhexadecylphosphoryl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 

Relevant academic research and scientific papers

Confirmation of the connectivity of 4,8,12,16,20-pentamethylpentacosylphoshoryl β-D-mannopyranoside, an unusual β-mannosyl phosphoisoprenoid from Mycobacterium avium, through synthesis

The synthesis of the title glycolipid is reported. Comparison of the electrospray and high-energy collision-induced dissociation mass spectra of the synthetic material with those reported for the isolate confirm the structure of this unusual antigenic substance with its modified isoprenoid chain.

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.