Pyrazinecarboxamide, 3,4-dihydro-3-oxo-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- (9CI)

Base Information

• Chemical Name: Pyrazinecarboxamide, 3,4-dihydro-3-oxo-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- (9CI)
• CAS No.: 499785-81-8
• Molecular Formula: C16H19N3O9
• Molecular Weight: 397.34
• Mol file: 499785-81-8.mol

Synonyms:PyrazinecarboxaMide, 3,4-dihydro-3-oxo-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- (9CI)

Chemical Property of Pyrazinecarboxamide, 3,4-dihydro-3-oxo-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- (9CI)

Chemical Property:

• PSA: 166.11000
• LogP: -0.63360

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pyrazinecarboxamide, 3,4-dihydro-3-oxo-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- (9CI)

There total 2 articles about Pyrazinecarboxamide, 3,4-dihydro-3-oxo-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)- (9CI) 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: 66.0%

3-oxo-3,4-dihydropyrazine-2-carboxamide (55321-99-8) + 1,2,3,5-tetraacetylribose (13035-61-5) → (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl] tetrahydro-3-furanyl acetate (499785-81-8)

Guidance literature:

3-oxo-3,4-dihydropyrazine-2-carboxamide; 1,2,3,5-tetraacetylribose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 1h; Reflux;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 2h;

DOI:10.3390/molecules25204813

Reference yield:

C8H13N3O2Si + 1,2,3,5-tetraacetylribose (13035-61-5) → (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl] tetrahydro-3-furanyl acetate (499785-81-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 3h;

Reference yield:

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl] tetrahydro-3-furanyl acetate (499785-81-8) → 4-(2'-C-methyl-β-D-ribofuranosyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide 5'-O-[phenyl-(benzyloxy-L-alaninyl)]phosphate

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol; sodium methylate / 0.5 h / 0 °C

2.1: 1-methyl-1H-imidazole; pyridine / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With pyridine; 1-methyl-1H-imidazole; methanol; sodium methylate; In tetrahydrofuran;

DOI:10.3390/molecules25204813

upstream raw materials:

1,2,3,5-tetraacetylribose

3-oxo-3,4-dihydropyrazine-2-carboxamide

Refernces

• 1、 -. "NOVEL VIRUS PROLIFERATION INHIBITION/VIRUCIDAL METHOD AND NOVEL PYRADINE NUCLEOTIDE/PYRADINE NUCLEOSIDE ANALOGUE". Page/Page column 72. . Retrieved 2010/02/06.