9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine

Base Information

• Chemical Name: 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine
• CAS No.: 1294481-82-5
• Molecular Formula: C25H19Cl3FN5O5
• Molecular Weight: 594.81
• Mol file: 1294481-82-5.mol

Synonyms:9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine;9-[(2R)-3,5-Bis-O-(4-chlorobenzoyl)-2-deoxy-2-fluoro-2-methyl-beta-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-amine

Chemical Property of 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine

Chemical Property:

• Melting Point: 171-176℃
• Boiling Point: 759.4±70.0 °C(Predicted)
• PKA: 1.69±0.10(Predicted)
• PSA: 131.45000
• Density: 1.63
• LogP: 5.65810
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99%, ^*data from raw suppliers

(2R,3R,4R,5R)-5-(2-Amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl4-chlorobenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine

There total 6 articles about 9-[(2R)-3,5-bis-O-(4-Chlorobenzoyl)-2-deoxy-2-fluoro-2-Methyl-b-D-erythro-pentofuranosyl]-6-chloro-9H-purin-2-aMine 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: 65.0%

(2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate (1294481-81-4) + 2-Amino-6-chloropurin (10310-21-1) → (2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate (1294481-82-5)

Guidance literature:

2-Amino-6-chloropurin; With potassium tert-butylate; In tert-butyl alcohol; at 20 ℃; for 0.5h; Inert atmosphere;

(2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate; In acetonitrile; tert-butyl alcohol; at 20 - 50 ℃; for 22.0833h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo200060f

Reference yield:

(2R,3R,4R,5R)-5-bromo-2-((4-chlorobenzoyl)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl-4-chlorobenzoate + 2-amino-6-chloropurine (10310-21-1) → (2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate (1294481-82-5) + (2R,3R,4R,5S) 5-(2-amino-6-chloro-9H-purin-9-yl)-2-((4-chlorobenzoyl)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl-4-chlorobenzoate

Guidance literature:

2-amino-6-chloropurine; With potassium tert-butylate; In tert-butyl alcohol; at 20 ℃; for 0.5h;

(2R,3R,4R,5R)-5-bromo-2-((4-chlorobenzoyl)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl-4-chlorobenzoate; In acetonitrile; tert-butyl alcohol; at 50 ℃; for 43h; Optical yield = 81.818 %de;

Reference yield:

((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate (1294481-79-0) → (2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate (1294481-82-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2.25 h / -30 - -10 °C / Inert atmosphere

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / -25 - -17 °C / Inert atmosphere

3.1: potassium tert-butylate / tert-butyl alcohol / 0.5 h / 20 °C / Inert atmosphere

3.2: 22.08 h / 20 - 50 °C / Inert atmosphere

With carbon tetrabromide; potassium tert-butylate; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo200060f

upstream raw materials:

((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate

((2R,3R,4R,5R)-3-((4-chlorobenzoyl)oxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate

(2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate

2-Amino-6-chloropurin

Downstream raw materials:

PSI-938

(2R,3R,4R,5R)-5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

6-ethoxy-9-((2S,4aR,6R,7R,7aR)-7-fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ(5)-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine

(2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

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