Guanosine, N-benzoyl-, 2',3',5'-triacetate

Base Information

• Chemical Name: Guanosine, N-benzoyl-, 2',3',5'-triacetate
• CAS No.: 66781-54-2
• Molecular Formula: C23H23N5O9
• Molecular Weight: 513.464
• Mol file: 66781-54-2.mol

Synonyms:

Chemical Property of Guanosine, N-benzoyl-, 2',3',5'-triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Guanosine, N-benzoyl-, 2',3',5'-triacetate

There total 5 articles about Guanosine, N-benzoyl-, 2',3',5'-triacetate 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: 95.0%

2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine (1234319-81-3) → 2',3',5'-tri-O-acetyl-N2-benzoylguanosine (66781-54-2)

Guidance literature:

With palladium on carbon; hydrogen; In tetrahydrofuran; ethanol; at 20 ℃;

DOI:10.1021/jo100808w

Reference yield: 41.0%

N2,O2',O3',O5'-tetrabenzoylguanosine (28288-50-8) + acetic anhydride (108-24-7) → 2',3',5'-tri-O-acetyl-N2-benzoylguanosine (66781-54-2)

Guidance literature:

N²,O^2',O^3',O^5'-tetrabenzoylguanosine; With sodium hydroxide; In methanol; water; at 20 ℃; for 12h;

acetic anhydride; With pyridine; dmap; at 0 - 20 ℃; for 12h;

DOI:10.1128/AAC.00443-17

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-benzoylamino-6-dimethylthiocarbamoyloxy-purin-9-yl)-tetrahydro-furan-3-yl ester (90742-11-3) → 2',3',5'-tri-O-acetyl-N2-benzoylguanosine (66781-54-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 5h; Product distribution; Ambient temperature; other protected carbamoylguanosine derivatives, other reagents, other solvents, other times, other temperatures;

DOI:10.1021/ja00328a042

upstream raw materials:

2',3',5'-tri-O-acetyl-2-N-benzoyl-6-O-benzylguanosine

N²,O^2',O^3',O^5'-tetrabenzoylguanosine

acetic anhydride

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-benzoylamino-6-dimethylthiocarbamoyloxy-purin-9-yl)-tetrahydro-furan-3-yl ester

Downstream raw materials:

Acetic acid (3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(2,4,6-triisopropyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(2,4,6-triisopropyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-benzoylamino-6-(diphenoxy-phosphoryloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester

3',5'-di-O-acetyl-N²-benzoylguanosine

Refernces

• 1、 Caner, Joaquim,Vilarrasa, Jaume. "15N double-labeled guanosine from inosine through ring-opening-ring-closing and one-pot Pd-catalyzed C-O and C-N cross-coupling reactions". supporting information; experimental part. p. 4880 - 4883. Retrieved 2010/10/19.
• 2、 Takaku, Hiroshi,Kamaike, Kazuo,Kasuga, Kenichi. "4-CHLOROPHENYL 5-CHLORO-8-QUINOLYL HYDROGEN PHOSPHATE: A USEFUL PHOSPHORYLATING AGENT FOR GUANOSINE 3'-PHOSPHOTRIESTER". . p. 197 - 200. Retrieved 2007/10/02.