ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

Base Information

• Chemical Name: ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate
• CAS No.: 1412427-19-0
• Molecular Formula: C₄₁H₅₈N₇O₁₂PSi
• Molecular Weight: 900.01
• Mol file: 1412427-19-0.mol

Synonyms:ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

Chemical Property of ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate

There total 5 articles about ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-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: 40.0%

(Sp)-ethyl 3-(2-(((((S)-1-ethoxy-1-oxopropan-2-yl)amino)(4-(methylsulfonyl)phenoxy)phosphoryl)oxy)phenyl)propanoate (1412427-17-8) + C25H36N6O6Si → ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate (1412427-19-0)

Guidance literature:

C₂₅H₃₆N₆O₆Si; With tert-butylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

(Sp)-ethyl 3-(2-(((((S)-1-ethoxy-1-oxopropan-2-yl)amino)(4-(methylsulfonyl)phenoxy)phosphoryl)oxy)phenyl)propanoate; In tetrahydrofuran; at -78 - 20 ℃; for 48h; Inert atmosphere;

Reference yield:

ethyl 3-(2-hydroxyphenyl)propanoate (20921-04-4) → ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate (1412427-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; trichlorophosphate / diethyl ether / 18 h / -78 - 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 7.33 h / -78 - 0 °C / Inert atmosphere

2.2: 12 h / -78 - 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

4.1: tert-butylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.2: 48 h / -78 - 20 °C / Inert atmosphere

With tert-butylmagnesium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane;

Reference yield:

C6H4(CH2CH2C(O)O) (119-84-6,1341-36-2) → ethyl 3-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-(((benzyloxy)carbonyl)amino)-9H-purin-9-yl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)((1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate (1412427-19-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sulfuric acid / 12 h / 0 °C / Inert atmosphere

1.2: pH 6 - 6.5

2.1: triethylamine; trichlorophosphate / diethyl ether / 18 h / -78 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 7.33 h / -78 - 0 °C / Inert atmosphere

3.2: 12 h / -78 - 20 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

5.1: tert-butylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.2: 48 h / -78 - 20 °C / Inert atmosphere

With sulfuric acid; tert-butylmagnesium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trichlorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane;

upstream raw materials:

C₆H₄(CH₂CH₂C(O)O)

ethyl 3-(2-hydroxyphenyl)propanoate

C₁₁H₁₃Cl₂O₄P

(Sp)-ethyl 3-(2-(((((S)-1-ethoxy-1-oxopropan-2-yl)amino)(4-(methylsulfonyl)phenoxy)phosphoryl)oxy)phenyl)propanoate

Downstream raw materials:

ethyl 3-(2-(((R)-(((2R,3R,4R,5R)-5-(2,6-diamino-9H-pu r in-9-y l )-3, 4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(((S)-1-ethoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)propanoate