N²-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine

Base Information

• Chemical Name: N²-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine
• CAS No.: 372515-48-5
• Molecular Formula: C₃₇H₃₉N₅O₉
• Molecular Weight: 697.745

Synonyms:N²-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine

Chemical Property of N²-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine

Chemical Property:

Purity/Quality:

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Technology Process of N²-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine

There total 7 articles about N²-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine 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:

N-(9-{7-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide → N2-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine (372515-48-5)

Guidance literature:

With acetic acid; In tetrahydrofuran; dichloromethane; at 20 ℃; for 13h;

DOI:10.1002/1522-2675(20010613)84:6<1778::AID-HLCA1778>3.0.CO;2-3

Reference yield:

L-arabinofuranose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2,36562-42-2) → N2-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine (372515-48-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 91.7 percent / pyridine / CH₂Cl₂ / 2.5 h

2: 58 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 21 h / 80 °C

3: 79 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

4: 66 percent / TMS-Cl / dimethylformamide / 16 h / 20 °C

5: 2,6-lutidine / CH₂Cl₂ / 120 h / 4 °C

6: aq. AcOH / CH₂Cl₂; tetrahydrofuran / 13 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; chloro-trimethyl-silane; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20010613)84:6<1778::AID-HLCA1778>3.0.CO;2-3

Reference yield:

1',2',3',4'-tetra-O-benzoyl-L-lyxopyranose (372515-38-3) → N2-isobutyryl-9-{3'-O-acetyl-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine (372515-48-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 58 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 21 h / 80 °C

2: 79 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

3: 66 percent / TMS-Cl / dimethylformamide / 16 h / 20 °C

4: 2,6-lutidine / CH₂Cl₂ / 120 h / 4 °C

5: aq. AcOH / CH₂Cl₂; tetrahydrofuran / 13 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; chloro-trimethyl-silane; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(20010613)84:6<1778::AID-HLCA1778>3.0.CO;2-3

upstream raw materials:

L-arabinofuranose

1',2',3',4'-tetra-O-benzoyl-L-lyxopyranose

N²-isobutyryl-9-(α-L-lyxopyranosyl)guanine

N²-isobutyryl-9-{2',3'-O-[methoxy(methyl)methylidene]-α-L-lyxopyranosyl}guanine

Downstream raw materials:

N²-isobutyryl-9-{3'-O-acetyl-2'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-4'-O-[(4'',4'''-dimethoxytriphenyl)methyl]-α-L-lyxopyranosyl}guanine

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