218271-99-9

Upstream product

• 219586-69-3 (Z)-N-<(2S,3S,4R)-4-N-tert-butoxycarbonylamine-2,3-O-isopropylidenedioxy-5-phenylpentylidene>benzylamine N-oxide 
• 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 

Downstream Products

• 218272-00-5 (3aS,4R,8S,8aS)-4,8-Dibenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 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 

Relevant academic research and scientific papers

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.

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