9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N²-acetylguanine

Base Information

• Chemical Name: 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N²-acetylguanine
• CAS No.: 783322-68-9
• Molecular Formula: C₂₆H₂₉N₅O₁₂S
• Molecular Weight: 635.609

Synonyms:9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N²-acetylguanine

Chemical Property of 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N²-acetylguanine

Chemical Property:

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Technology Process of 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N²-acetylguanine

There total 8 articles about 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N²-acetylguanine 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:

4-Methyl-benzoic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(2-acetylamino-6-diphenylcarbamoyloxy-purin-9-yl)-5-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester → 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N2-acetylguanine (783322-68-9)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.5h;

DOI:10.1021/ja048417i

Reference yield:

N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N2-acetylguanine (783322-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.5 h / 80 °C

1.2: SnCl₄ / 1,2-dichloro-ethane / 3 h / 70 °C

2.1: 1.6 g / aq. TFA / 0.5 h / 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; trifluoroacetic acid; In 1,2-dichloro-ethane;

DOI:10.1021/ja048417i

Reference yield:

6-O-(4-toluoyl)-1,2:3,4-di-O-isopropylidene-β-D-psicofuranose (344905-99-3) → 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N2-acetylguanine (783322-68-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 60 percent / HCl

2.1: pyridine / 12 h / 4 °C

3.1: aq. TFA / 0.42 h / 20 °C

4.1: 5.3 g / pyridine / 3 h / 20 °C

5.1: HBr; AcOH / CH₂Cl₂ / 12 h / 0 - 20 °C

6.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.5 h / 80 °C

6.2: SnCl₄ / 1,2-dichloro-ethane / 3 h / 70 °C

7.1: 1.6 g / aq. TFA / 0.5 h / 20 °C

With pyridine; hydrogenchloride; N,O-bis-(trimethylsilyl)-acetamide; hydrogen bromide; acetic acid; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ja048417i

upstream raw materials:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

6-O-(4-toluoyl)-1,2:3,4-di-O-isopropylidene-β-D-psicofuranose

4-Methyl-benzoic acid (2R,3R,4R)-3,4-diacetoxy-5-bromo-5-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester

2-O-methyl-3,4-O-isopropylidene-6-O-(4-toluoyl)-D-psicofuranose

Downstream raw materials:

9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N²-(N,N-(dimethylamino)methylene)guanine

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