N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Base Information

• Chemical Name: N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide
• CAS No.: 132849-69-5
• Molecular Formula: C₁₇H₁₆FN₅O₄
• Molecular Weight: 373.344
• Mol file: 132849-69-5.mol

Synonyms:N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Chemical Property of N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

There total 4 articles about N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 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:

(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol (20535-16-4) + benzoyl chloride (98-88-4) → N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (132849-69-5)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1002/hlca.19910740104

Reference yield:

9-((2R,3S,4S,5R)-4-fluoro-3-(trityloxy)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)-N-trityl-9H-purin-6-amine → N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (132849-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C

2.1: pyridine; chloro-trimethyl-silane / 0.25 h / 0 - 20 °C

2.2: 4 h / 20 °C

With pyridine; chloro-trimethyl-silane; trifluoroacetic acid; In dichloromethane;

Reference yield:

(2R,3R,4R,5R)-2-(hydroxymethyl)-5-(6-(tritylamino)-9H-purin-9-yl)-4-(trityloxy)tetra-hydrofuran-3-ol (137965-10-7) → N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (132849-69-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: pyridine; diethylamino-sulfur trifluoride / chloroform / 15 h / 0 - 20 °C

3.1: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C

4.1: pyridine; chloro-trimethyl-silane / 0.25 h / 0 - 20 °C

4.2: 4 h / 20 °C

With pyridine; chloro-trimethyl-silane; 2,6-di-tert-butyl-pyridine; diethylamino-sulfur trifluoride; silver trifluoromethanesulfonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform;

upstream raw materials:

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

benzoyl chloride

(2R,3R,4R,5R)-2-(hydroxymethyl)-5-(6-(tritylamino)-9H-purin-9-yl)-4-(trityloxy)tetra-hydrofuran-3-ol

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine

Downstream raw materials:

N⁶-Benzoyl-9-<3'-deoxy-3'-fluoro-5'-O-(monomethoxytrityl)-β-D-xylofuranosyl>adenine

9-<2-O-Benzoyl-3-fluoro-3-deoxy-5-O-(monomethoxytrityl)-β-D-xylofuranosyl>-N⁶,N⁶-dibenzoyladenine

9-<3-Fluoro-3-deoxy-5-O-(monomethoxytrityl)-β-D-xylofuranosyl>-N⁶-benzoyladenine 2'-<2-chlorophenyl 2-(4-nitrophenyl)ethyl phosphate>

9-(2-O-Benzoyl-3-fluoro-3-deoxy-β-D-xylofuranosyl)-N⁶,N⁶-dibenzoyladenine