N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

Base Information

Chemical Name:N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide
CAS No.:1403480-89-6
Molecular Formula:C₃₇H₄₇FN₄O₈S
Molecular Weight:726.867
Hs Code.:

N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

Synonyms:N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

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Chemical Property of N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

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Technology Process of N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

There total 12 articles about N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide 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: 82.0%

: 1403480-79-4
tert-butyl (2-(((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)carbamoyl)-4-nitrophenyl)(but-3-en-1-yl)carbamate

: 1403480-89-6
N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

Guidance literature:: tert-butyl (2-(((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)carbamoyl)-4-nitrophenyl)(but-3-en-1-yl)carbamate; With 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; In dichloromethane; at 0 - 20 ℃; Cooling with ice; Inert atmosphere;

With pyridine hydrofluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield:

: C₄₄H₆₁FN₄O₁₀SSi

: 1403480-89-6
N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/jm500994n

Reference yield:

: C₃₀H₅₆N₂O₆Si₂

: 1403480-89-6
N-((2R,3R)-3-(allyloxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-(but-3-en-1-ylamino)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzamide

Guidance literature:: Multi-step reaction with 10 steps

1: potassium carbonate / tetrahydrofuran; methanol; water / 3 h / 20 °C

2: 2,6-dimethylpyridine / dichloromethane / 18 h / 20 °C

3: dimethylsulfide borane complex / tetrahydrofuran / 6.25 h / 0 - 65 °C / Inert atmosphere

4: triethylamine / dichloromethane / 3.5 h / 0 - 20 °C

5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 7 h / 20 - 35 °C

6: dmap / tetrahydrofuran / 1 h / Reflux

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h

8: sodium hydride / N,N-dimethyl-formamide / 0 °C

9: 2,6-dimethylpyridine / dichloromethane / 11 h / 0 - 20 °C / Inert atmosphere

10: pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm500994n