219586-75-1

Upstream product

• 153223-10-0 (2R,3S,4S,5R)-2,5-bis[N-(benzyloxycarbonyl)amino]-1,6-diphenyl-3,4-hexanediol 
• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 
• 219586-73-9 (2R,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol 
• 219586-67-1 (Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide 
• 882525-50-0 (3E,2R,5R)-N,N'-bis-(tert-butylsulfonyl)-1,6-diphenylhex-3-ene-2,5-diamine 
• 882525-48-6 (R)-2-benzyl-1-(tert-butylsulfonyl)-aziridine 
• 219586-71-7 (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol 
• 170870-15-2 (1R,1'R)-1,1'-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethanamine) 

Downstream Products

• 310441-11-3 (2R,3S,4S,5R)-2,5-bis(dimethylamino)-1,6-diphenyl-3,4-hexanediol 
• 1312443-45-0 (4R,5S)-5-((1S,2R)-2-amino-1-hydroxy-3-phenylpropyl)-4-benzyloxazolidin-2-one 
• 153223-11-1 (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one 
• 170870-15-2 (1R,1'R)-1,1'-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethanamine) 

Relevant academic research and scientific papers

Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450

Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

Dimerization of lithiated terminal aziridines

Let's get together: Dimerization of enantiopure terminal aziridines by lithiation gives efficiently N-protected 2-ene-1,4-diamines with complete selectivity for the E olefin (see scheme). The usefulness of the method was demonstrated in a concise synthesis of (R,S,S,R)-2,5-diamino-1,6-diphenylhexane- 3,4-diol, the core unit of many extremely potent HIV protease inhibitors and also asymmetric catalysts. (Chemical Equation Presented).

Grignard addition to aldonitrones. Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols

A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4- diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from β- amino-α-hydroxy aldehydes followed by reduction of the resulting N- benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3- diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV- 1 protease inhibitors.