N⁹-(3'-Deoxy-β-D-glucopyranosyl)guanin

Base Information

• Chemical Name: N⁹-(3'-Deoxy-β-D-glucopyranosyl)guanin
• CAS No.: 145593-93-7
• Molecular Formula: C₁₅H₂₁N₅O₆
• Molecular Weight: 367.362
• Mol file: 145593-93-7.mol

Synonyms:

Chemical Property of N⁹-(3'-Deoxy-β-D-glucopyranosyl)guanin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁹-(3'-Deoxy-β-D-glucopyranosyl)guanin

There total 1 articles about N⁹-(3'-Deoxy-β-D-glucopyranosyl)guanin 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:

2-N-isobutyrylguanine (21047-89-2) + 1,2,4,6-Tetra-O-benzoyl-3-deoxy-β-D-ribo-hexopyranose (145593-91-5) → N9-(3'-Deoxy-β-D-glucopyranosyl)guanin (145593-93-7) + N7-(3'-Deoxy-β-D-glucopyranosyl)guanin

Guidance literature:

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; Yield given; 1) acetonitrile, 80 deg C, 16 h, 2) THF/MeOH/H₂O (5:4:1), 0 deg C, 25 min;

DOI:10.1002/hlca.19920750503

Reference yield:

N9-(3'-Deoxy-β-D-glucopyranosyl)guanin (145593-93-7) → 9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N2-isobutyrylguanin (145594-09-8,145610-79-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / pyridine / dimethylformamide / 3 h / Ambient temperature

3: 69 percent / (i-Pr)2EtN / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19920750503

Reference yield:

N9-(3'-Deoxy-β-D-glucopyranosyl)guanin (145593-93-7) → 9-<2',3'-Dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>-N2-isobutyrylguanin (145594-11-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / pyridine / dimethylformamide / 3 h / Ambient temperature

3: 4-(dimethylamino)pyridine, pyridine / 20 h / Ambient temperature

4: pyridine, N,N'-dicyclohexylcarbodiimide / dioxane / 3 h / Ambient temperature

With pyridine; dmap; dicyclohexyl-carbodiimide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19920750503

upstream raw materials:

2-N-isobutyrylguanine

1,2,4,6-Tetra-O-benzoyl-3-deoxy-β-D-ribo-hexopyranose

Downstream raw materials:

9-(2',3'-Dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl)-N²-isobutyrylguanin

Succinic acid mono-[(2R,3S,6R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-pyran-3-yl] ester

9-<4'-O-<(2-Cyanoethoxy)(diisopropylamino)phosphino>-2',3'-dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin

9-<2',3'-Dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-4'-O-<4-O-(4-nitrophenyl)succinyl>-β-D-glucopyranosyl>-N²-isobutyrylguanin