[9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester
• CAS No.: 357928-60-0
• Molecular Formula: C₂₂H₂₄N₆O₆
• Molecular Weight: 468.469
• Mol file: 357928-60-0.mol

Synonyms:[9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester

Chemical Property of [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester

There total 2 articles about [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester 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%

1-((benzyloxy)carbonyl)-3-methylimidazolium tetrafluoroborate + 5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-51-5) → [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester (357928-60-0)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; acetonitrile; at 20 ℃; for 22h;

DOI:10.1021/ol015995k

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester (357928-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / BOP; 1-hydroxybenzotriazole hydrate / dimethylformamide / 4 h / 20 °C

2: 66 percent / NaHCO₃ / acetonitrile; CH₂Cl₂ / 22 h / 20 °C

With sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1-hydroxybenzotriazol-hydrate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol015995k

Reference yield: 50.0%

3-chloro-3-oxopropanoic acid methyl ester (37517-81-0) + [9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester (357928-60-0) → 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-3-oxo-propionic acid methyl ester (357928-62-2)

Guidance literature:

In toluene; at 110 ℃;

DOI:10.1021/ol015995k

upstream raw materials:

5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine

2',3'-isopropylideneadenosine-5'-carboxylic acid

Downstream raw materials:

3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-3-oxo-propionic acid methyl ester

3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester