N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine

Base Information

• Chemical Name: N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine
• CAS No.: 144924-99-2
• Molecular Formula: C17H16FN5O4
• Molecular Weight: 373.344
• Mol file: 144924-99-2.mol

Synonyms:N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine

Chemical Property of N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine

Chemical Property:

• PSA: 122.39000
• Density: 1.67±0.1 g/cm3(Predicted)
• LogP: 0.74030

Purity/Quality:

97% ^*data from raw suppliers

N-(9-((2R,3S,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine

There total 10 articles about N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine 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: 86.7%

N6-benzoyl-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (135473-17-5) → N-(9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (144924-99-2)

Guidance literature:

With water; sodium hydroxide; In pyridine; methanol; at -5 - 0 ℃; for 0.5h;

Reference yield: 85.0%

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (20187-82-0,20227-41-2,64183-27-3,123334-75-8) + benzoyl chloride (98-88-4) → N-(9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (144924-99-2)

Guidance literature:

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine; With pyridine; chloro-trimethyl-silane;

benzoyl chloride;

With ammonia; water;

Reference yield:

C21H20FN5O6 → C19H18FN5O5 + N-(9-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide (144924-99-2)

Guidance literature:

With Amano lipase, Burkholderia cepacia, PS; In aq. phosphate buffer; dimethyl sulfoxide; at 20 ℃; for 20h; pH=6.8; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/acs.oprd.1c00026

upstream raw materials:

9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine

benzoyl chloride

N-benzoyladenine

N⁶-benzoyl-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine

Downstream raw materials:

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

C₂₇H₃₄FN₇O₅

C₂₉H₄₄FN₅O₄Si₂

C₂₃H₂₈FN₅O₅Si

Refernces

• 1、 Siler, David A.,Calimsiz, Selcuk,Doxsee, Ian J.,Kwong, Bernard,Ng, Jeffrey D.,Sarma, Keshab,Shen, Jinyu,Curl, Jonah W.,Davy, Jason A.,Garber, Jeffrey A. O.,Ha, Sura,Lapina, Olga,Lee, Jisung,Lin, Lennie,Park, Sangsun,Rosario, Mary,St-Jean, Olivier,Yu, Guojun. "Synthesis of Rovafovir Etalafenamide (Part IV): Evolution of the Synthetic Process to the Fluorinated Nucleoside Fragment". . p. 1263 - 1274. Retrieved 2021/05/29.
• 2、 -. "INHIBITORS OF S-ADENOSYL-L-METHIONINE DECARBOXYLASE". Page/Page column 15; 22-23. . Retrieved 2009/01/23.