(2S)-isopropyl 2-(((((2R,3R_.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate

Base Information

• Chemical Name: (2S)-isopropyl 2-(((((2R,3R_.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate
• CAS No.: 1365634-49-6
• Molecular Formula: C₂₂H₃₀N₃O₉PS
• Molecular Weight: 543.535

Synonyms:(2S)-isopropyl 2-(((((2R,3R_.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate

Chemical Property of (2S)-isopropyl 2-(((((2R,3R_.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate

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Technology Process of (2S)-isopropyl 2-(((((2R,3R_.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate

There total 4 articles about (2S)-isopropyl 2-(((((2R,3R_.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate 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:

2'-methyluridine (1365634-47-4) → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate (1365634-50-9) + (2S)-isopropyl 2-(((((2R,3R.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate (1365634-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: water; formic acid / 1.5 h / 50 °C

2: chiral PAK AD / carbon dioxide; methanol / Resolution of racemate

With formic acid; water; In methanol; carbon dioxide;

Reference yield:

2'-C-methyluridine 5'-(O-phenyl-N-(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate (1365634-48-5) → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate (1365634-50-9) + (2S)-isopropyl 2-(((((2R,3R.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate (1365634-49-6)

Guidance literature:

With chiral PAK AD; In methanol; carbon dioxide; Resolution of racemate;

Reference yield:

(2S)-isopropyl 2-((phenoxy(pyridin-2-ylthio)phosphorothioyl)amino)propanoate + 2'-C-methyluridine (31448-54-1) → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate (1365634-50-9) + (2S)-isopropyl 2-(((((2R,3R.4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorothioyl)amino)propanoate (1365634-49-6)

Guidance literature:

With trifluorormethanesulfonic acid; In 1,4-dioxane; at 23 ℃; Solvent; Overall yield = 80 %; diastereoselective reaction; Large scale;

upstream raw materials:

2'-methyluridine

2'-methyluridine

2'-C-methyluridine 5'-(O-phenyl-N-(S)-1-(isopropoxycarbonyl)ethyl)thiophosphoramidate

2'-C-methyluridine

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