5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine
• CAS No.: 873556-49-1
• Molecular Formula: C₂₇H₃₀N₆O₇S
• Molecular Weight: 582.637
• Mol file: 873556-49-1.mol

Synonyms:5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

Chemical Property of 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine

There total 6 articles about 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine 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: 48.0%

((3aR,4R,6R,6aR)-6-(6-((tert-butoxycarbonyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (873556-35-5) + 2-bromomethylphenyl benzyl ether (103633-30-3) → 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine (873556-49-1) + C41H42N6O8S

Guidance literature:

With caesium carbonate; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 16h;

Reference yield: 48.0%

2-bromomethylphenyl benzyl ether (103633-30-3) + ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (112921-00-3) → 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine (873556-49-1)

Guidance literature:

With caesium carbonate; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm051060o

Reference yield:

2-methyl-benzyl alcohol (89-95-2) → 5'-O-(N-(2-benzyloxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine (873556-49-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / K₂CO₃ / acetone / 5 h / Heating

2: 98 percent / NaBH₄ / methanol / 0.5 h / 20 °C

3: 88 percent / PPh₃; CBr₄ / CH₂Cl₂ / 0.5 h

4: 48 percent / Cs₂CO₃ / CH₂Cl₂; dimethylformamide / 16 h / 20 °C

With sodium tetrahydroborate; carbon tetrabromide; potassium carbonate; caesium carbonate; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm051060o

upstream raw materials:

2-bromomethylphenyl benzyl ether

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

2-methyl-benzyl alcohol

2-benzyloxybenzyl alcohol

Downstream raw materials:

5'-O-(N-(2-hydroxybenzyl)sulfamoyl)-2',3'-O-isopropylideneadenosine