(S)-3-(N₂,N₆-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid

Base Information

• Chemical Name: (S)-3-(N₂,N₆-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid
• CAS No.: 1389321-44-1
• Molecular Formula: C₂₉H₃₃N₆O₈P
• Molecular Weight: 624.59

Synonyms:(S)-3-(N₂,N₆-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid

Chemical Property of (S)-3-(N₂,N₆-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid

Chemical Property:

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Technology Process of (S)-3-(N₂,N₆-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid

There total 2 articles about (S)-3-(N₂,N₆-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic 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: 80.0%

diisopropyl (S)-N2,N6-dibenzoyl-9-[3-hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (1374997-62-2) → (S)-3-(N2,N6-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid (1389321-44-1)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 20 ℃; for 24h; pH=6.7; aq. phosphate buffer;

DOI:10.1016/j.tet.2012.03.066

Reference yield:

diisopropyl {[(1S)-2-(2,6-diamino-9H-purin-9-yl)-1-(hydroxymethyl)ethyl]oxy}methylphosphonate (1374997-60-0) + benzoyl chloride (98-88-4) → (S)-3-(N2,N6-dibenzoyl-2,6-diamino-9H-purin-9-yl)-2-[(diisopropylphosphono)methoxy]propanoic acid (1389321-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; trimethylsilyl bromide / 0.5 h

1.2: 2 h / 20 °C

1.3: 0.5 h / 20 °C

2.1: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 24 h / 20 °C / pH 6.7 / aq. phosphate buffer

With pyridine; sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl bromide; In acetonitrile;

DOI:10.1016/j.tet.2012.03.066

upstream raw materials:

diisopropyl {[(1S)-2-(2,6-diamino-9H-purin-9-yl)-1-(hydroxymethyl)ethyl]oxy}methylphosphonate

benzoyl chloride

diisopropyl (S)-N₂,N₆-dibenzoyl-9-[3-hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine

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