218271-99-9

Upstream product

• 218271-90-0 (+)-(4R,5R)-1-(2,2-dimethyl-5-phenylacetyl-[1,3]dioxolan-4-yl)-2-phenylethanone 
• 207561-63-5 (2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol 
• 219586-74-0 (2S,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol 
• 218271-92-2 (3S,4S)-2,5-bis(methoxyimino)-1,6-diphenyl-3,4-O-isopropylidenehexanediol 
• 219586-69-3 (Z)-N-<(2S,3S,4R)-4-N-tert-butoxycarbonylamine-2,3-O-isopropylidenedioxy-5-phenylpentylidene>benzylamine N-oxide 

Downstream Products

• 207561-64-6 (2R,3S,4S,5S)-2,5-diamino-1,6-diphenyl-3,4-hexanediol 
• 218272-12-9 (3aS,4S,8R,8aS)-4,5,7,8-Tetrabenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 218272-01-6 (4S,5S,6S,7R)-1,3,4,7-Tetrabenzyl-5,6-dihydroxy-[1,3]diazepan-2-one 
• 218272-00-5 (3aS,4R,8S,8aS)-4,8-Dibenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 

Relevant academic research and scientific papers

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.

Stereoisomers of cyclic urea HIV-1 protease inhibitors: Synthesis and binding affinities

We have synthesized stereoisomers of cyclic urea HIV-1 protease inhibitors to study the effect of varying configurations on binding affinities. Four different synthetic approaches were used to prepare the desired cyclic urea stereoisomers. The original cy

Synthesis of C2-symmetric dibenzyldiamino diols by double stereoselective grignard addition to (S,S)-tartraldehyde dinitrone

A new asymmetric two-dimensional synthesis of 1,4-diamino 2,3-diols is illustrated by double addition of benzylmagnesium chloride to the bis- nitrone derived from (R,R)-tartraldehyde and reduction of the resulting dihydroxylamines.