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

Base Information

• Chemical Name: 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
• CAS No.: 1412427-10-1
• Molecular Formula: C₂₇H₃₈N₇O₁₀P
• Molecular Weight: 651.613
• Mol file: 1412427-10-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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: 91.0%

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) → 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 (1412427-10-1)

Guidance literature:

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; With hydrogenchloride; In diethyl ether; acetonitrile; at 0 - 20 ℃; for 48h;

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 12.5h; under 760.051 Torr;

Reference yield: 41.0%

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 → 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 (1412427-10-1)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jm501874e

Reference yield:

ethyl 3-(2-hydroxyphenyl)propanoate (20921-04-4) → 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 (1412427-10-1)

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 / 18 h / -78 - 20 °C / Inert atmosphere

3.1: triethylamine / diethyl ether / 16.5 h / 0 °C

4.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere

4.2: 72 h / 20 °C

4.3: 4 h / 20 °C / pH 7

With tert-butylmagnesium chloride; triethylamine; 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