L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester

Base Information

• Chemical Name: L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester
• CAS No.: 1334513-10-8
• Molecular Formula: C22H30FN4O8P
• Molecular Weight: 528.474
• Mol file: 1334513-10-8.mol

Synonyms:L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester;N-[[P(S),2'R]-2'-Deoxy-2'-fluoro-2'-methyl-P-phenyl-5'-cytidylyl]-L-alanine 1-methylethyl ester

Chemical Property of L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

SofosbuvirimpurityJ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester

There total 3 articles about L-Alanine, N-[[P(S),2'R]-2'-deoxy-2'-fluoro-2'-Methyl-P-phenyl-5'-cytidylyl]-, 1-Methylethyl ester 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: 71.0%

(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine (817204-33-4) + (S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester (1334513-02-8,1627824-09-2) → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate (1334513-10-8)

Guidance literature:

With pyridine; dimethylaluminum chloride; In hexane; at 0 - 4 ℃; for 24h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00469

Reference yield:

O-phenyl phosphorodichloridate (770-12-7) → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate (1334513-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0.25 h / -70 °C

1.2: 4.5 h / -70 - 0 °C

1.3: 4.33 h / 0 °C

2.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.55 h / 20 °C

2.2: 18.05 h / 20 °C

With tert-butylmagnesium chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo201492m

Reference yield:

alanine isopropyl ester hydrochloride (39613-92-8,62062-56-0,62062-65-1) → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate (1334513-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0.25 h / -70 °C

1.2: 4.5 h / -70 - 0 °C

1.3: 4.33 h / 0 °C

2.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.55 h / 20 °C

2.2: 18.05 h / 20 °C

With tert-butylmagnesium chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo201492m

upstream raw materials:

(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine

(S)-2-[(S)-((2,3,4,5,6-pentafluorophenoxy)(phenoxy)phosphoryl)amino]propionic acid isopropyl ester

O-phenyl phosphorodichloridate

alanine isopropyl ester hydrochloride

Refernces

• 1、 Simmons, Bryon,Liu, Zhuqing,Klapars, Artis,Bellomo, Ana,Silverman, Steven M.. "Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189". supporting information. p. 2218 - 2221. Retrieved 2017/05/12.