(S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

Base Information

Chemical Name:(S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid
CAS No.:901776-10-1
Molecular Formula:C₂₃H₂₈N₈O₇
Molecular Weight:528.525
Hs Code.:

Synonyms:(S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

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Chemical Property of (S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

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Technology Process of (S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

There total 4 articles about (S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 43.0%

: tert-butyl (2S)-4-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)((E)-3-(2-nitrophenyl)allyl)amino)-2-((tert-butoxycarbonyl)amino)butanoate

: 901776-10-1
(S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 2h;
DOI:10.1021/acs.jmedchem.1c01094

Reference yield: 36.0%

: 901776-53-2
benzyl (S)-1-(tert-butoxycarbonyl)-3-(N-(2-nitrocinnamyl)-N-(((3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-tetrahydro-2,2-dimethylfuro[3,4-d][1,3]dioxol-6-yl)methyl)amino)propylcarbamate

: 901776-10-1
(S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

Guidance literature:: With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; at 0 - 20 ℃; for 18.5h;

Reference yield:

: 552-89-6
2-nitro-benzaldehyde

: 901776-10-1
(S)-4-(N-(2-nitrocinnamyl)-N-(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-tetrahydro-3,4-dihydroxyfuran-2-yl)methyl)amino)-2-aminobutanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: toluene / 80 °C

2: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane; water / 2 h / 20 °C

With sodium tris(acetoxy)borohydride; acetic acid; trifluoroacetic acid; In dichloromethane; water; 1,2-dichloro-ethane; toluene;
DOI:10.1021/acs.jmedchem.1c01094