O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine

Base Information

• Chemical Name: O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine
• CAS No.: 745822-42-8
• Molecular Formula: C₄₉H₅₅N₅O₁₁
• Molecular Weight: 890.003

Synonyms:O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine

Chemical Property of O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine

Chemical Property:

Purity/Quality:

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Technology Process of O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine

There total 7 articles about O⁶-benzyl-N²-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine 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: 73.0%

8-[(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]-2',3',5,'-tri-O6-benzoyl-N2-(2-methylpropanoyl)guanosine (745822-41-7) → O6-benzyl-N2-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine (745822-42-8)

Guidance literature:

With potassium carbonate; In methanol; water; at 0 - 20 ℃;

DOI:10.1002/hlca.200490118

Reference yield:

2,4-diamino-6-(benzyloxy)-5-nitrosopyrimidine (101724-61-2) → O6-benzyl-N2-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine (745822-42-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: DMF; oxalyl chloride / benzene / 3 h / 25 °C

1.2: 81 percent / pyridine / tetrahydrofuran / -60 - 23 °C

2.1: 90 percent / 1,2-bis(diphenylphosphino)ethane / o-xylene / 2 h / Heating

3.1: 80 percent / toluene / 24 h / Heating

4.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.42 h / 80 °C

4.2: 76 percent / TMSOTf / acetonitrile / 23 - 65 °C

5.1: 73 percent / K₂CO₃ / methanol; H₂O / 0 - 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; 1,2-bis-(diphenylphosphino)ethane; In methanol; o-xylene; water; toluene; acetonitrile; benzene;

DOI:10.1002/hlca.200490118

Reference yield:

NU6038 (100061-59-4) → O6-benzyl-N2-(2-methylpropanoyl)-8-[(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]guanosine (745822-42-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / NaNO₂ / acetic acid; H₂O / 80 °C

2.1: DMF; oxalyl chloride / benzene / 3 h / 25 °C

2.2: 81 percent / pyridine / tetrahydrofuran / -60 - 23 °C

3.1: 90 percent / 1,2-bis(diphenylphosphino)ethane / o-xylene / 2 h / Heating

4.1: 80 percent / toluene / 24 h / Heating

5.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.42 h / 80 °C

5.2: 76 percent / TMSOTf / acetonitrile / 23 - 65 °C

6.1: 73 percent / K₂CO₃ / methanol; H₂O / 0 - 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; 1,2-bis-(diphenylphosphino)ethane; sodium nitrite; In methanol; o-xylene; water; acetic acid; toluene; acetonitrile; benzene;

DOI:10.1002/hlca.200490118

upstream raw materials:

8-[(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-mannopyranosyl)methyl]-2',3',5,'-tri-O⁶-benzoyl-N²-(2-methylpropanoyl)guanosine

2,4-diamino-6-(benzyloxy)-5-nitrosopyrimidine

NU₆₀₃₈

benzyl alcohol

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