A synthesis of the HIV-protease inhibitor nelfinavir from d-tartaric acid

Synthesis of a Novel Benzoyl Adenosine Analog Containing a 1, 4-Dioxane Sugar Analog and the Synthesis of a Corresponding Uracil Adenine Dinucleotide

“…The tartrate was first converted into the corresponding enantiomerically pure diethyl ( 2R , 3R )-2- O -allyltartrate either by the reaction with allyl bromide in the presence of silver oxide or in a tin assisted reaction with dibutyltin oxide [9,10,11]. The allyl ether was reduced by LiAlH 4 [12,13,14] or NaBH 4 [15,16] to give a triol which was protected as an acetal with 2,2-dimethoxy-propane in the presence of p- toluene sulfonic acid. Subsequent ozonolysis afforded 1,4-dioxane sugar analog 3 which was further transformed into acetate 4 with acetic anhydride (Scheme 1).…”

Enantioselective Synthesis of Homo-N-Nucleosides Containing a 1,4-Dioxane Sugar Analog

“…Thus, (2 R ,3 R )-dimethyl tartrate was converted into the corresponding enantiomerically pure allyl ether 1 [ 9 ] either by the reaction with allyl bromide in the presence of silver oxide [ 10 ] or in a tin assisted reaction with dibutyltin oxide [ 11 , 12 ]. The dimethyl (2 R ,3 R )-2- O -allyltartrate 1 was then reduced by LiAlH 4 [ 13 , 14 , 15 ] or NaBH 4 [ 16 , 17 ] to give triol 2 . The two vicinal hydroxyl groups in 2 were next protected through formation of acetal 3 by the reaction with 2,2-dimethoxypropane in the presence of p- toluenesulfonic acid ( Scheme 1 ).…”

Biocatalytic routes to anti-viral agents and their synthetic intermediates

“…Most routes instead involve the use of protected 3-aminobutane-1,2,4-triol (ABT, 138, Scheme 30). [208][209][210] Suitably protected equivalents of ABT could be obtained efficiently through biocatalytic resolution. Faure and co-workers employed either singlestep or two-step lipase-catalysed resolution of N-protected ABT to obtain (2S,3R)-144 from 143 (Scheme 31A).…”

“…Although constituting a very attractive cascade, no enantiomeric and/or diastereomeric purity was reported, the transaminase Scheme 30 Synthesis of nelfinavir from suitably protected 3-aminobutane-1,2,4-triol (ABT) as described by Uchida et al (I), 208 Cho and co-workers (II) 209 and Borer et al 210 Scheme 31 Resolution of protected ABT derivatives 143 (A) 211 and 145/ 146 (B). 212 PPL: porcine pancreas lipase, PFL: Amano AK lipase (P. fluorescens), BCL: Amano PS lipase (Burkholderia cepacia) and BCL-C II: BCL immobilised on ceramic instead of diatomite.…”