isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

Base Information

• Chemical Name: isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate
• CAS No.: 1412427-51-0
• Molecular Formula: C₂₉H₄₂N₇O₁₀P
• Molecular Weight: 679.667

Synonyms:isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

Chemical Property of isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

Chemical Property:

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Technology Process of isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

There total 5 articles about isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)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:

C29H40N9O10P (1422526-26-8) → isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate (1412427-51-0)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In isopropyl alcohol; at 20 - 80 ℃; for 11h; Inert atmosphere;

DOI:10.1080/15257770.2019.1671594

Reference yield:

C6H4(CH2CH2C(O)O) (119-84-6,1341-36-2) → isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate (1412427-51-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / 20 °C / Inert atmosphere; Large scale

1.2: pH 6.5 - 7 / Large scale

2.1: trichlorophosphate / tert-butyl methyl ether / 15 - 30 °C

3.1: triethylamine / tert-butyl methyl ether; dichloromethane / 2 h / 20 °C

4.1: triethylamine / dichloromethane / 2 h / 0 - 30 °C / Large scale

5.1: tert-butylmagnesium chloride / tetrahydrofuran / 6 h / 0 - 30 °C / Inert atmosphere; Large scale

6.1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 65 - 80 °C / Inert atmosphere

7.1: hydrogen; 20% palladium hydroxide-activated charcoal / isopropyl alcohol / 11 h / 20 - 80 °C / Inert atmosphere

With sodium azide; sulfuric acid; 20% palladium hydroxide-activated charcoal; tert-butylmagnesium chloride; hydrogen; tetra-(n-butyl)ammonium iodide; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1080/15257770.2019.1671594

Reference yield:

isopropyl 3-(2-hydroxyphenyl)propanoate (20921-06-6) → isopropyl 3-(2-(((((2 R,3R,4R,5R)-5-(2,6-diamino-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate (1412427-51-0)

Guidance literature:

Multi-step reaction with 6 steps

1: trichlorophosphate / tert-butyl methyl ether / 15 - 30 °C

2: triethylamine / tert-butyl methyl ether; dichloromethane / 2 h / 20 °C

3: triethylamine / dichloromethane / 2 h / 0 - 30 °C / Large scale

4: tert-butylmagnesium chloride / tetrahydrofuran / 6 h / 0 - 30 °C / Inert atmosphere; Large scale

5: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 65 - 80 °C / Inert atmosphere

6: hydrogen; 20% palladium hydroxide-activated charcoal / isopropyl alcohol / 11 h / 20 - 80 °C / Inert atmosphere

With sodium azide; 20% palladium hydroxide-activated charcoal; tert-butylmagnesium chloride; hydrogen; tetra-(n-butyl)ammonium iodide; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1080/15257770.2019.1671594

upstream raw materials:

C₂₉H₄₀N₉O₁₀P

C₆H₄(CH₂CH₂C(O)O)

isopropyl 3-(2-hydroxyphenyl)propanoate

C₁₂H₁₅Cl₂O₄P

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