9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N⁶-benzoyladenine

Base Information

• Chemical Name: 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N⁶-benzoyladenine
• CAS No.: 478487-96-6
• Molecular Formula: C₃₁H₃₁N₅O₁₁S
• Molecular Weight: 681.68

Synonyms:9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N⁶-benzoyladenine

Chemical Property of 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N⁶-benzoyladenine

Chemical Property:

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Technology Process of 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N⁶-benzoyladenine

There total 6 articles about 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N⁶-benzoyladenine 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-benzoyladenine (4005-49-6) + 4-Methyl-benzoic acid (2R,3R,4R)-3,4-diacetoxy-5-bromo-5-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester (478487-98-8) → 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N6-benzoyladenine (478487-96-6)

Guidance literature:

N-benzoyladenine; With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; at 120 ℃; for 12h;

4-Methyl-benzoic acid (2R,3R,4R)-3,4-diacetoxy-5-bromo-5-methanesulfonyloxymethyl-tetrahydro-furan-2-ylmethyl ester; With tin(IV) chloride; In 1,2-dichloro-ethane; acetonitrile; at 70 ℃; for 3h;

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]-N6-benzoyladenine (478487-96-6)

Guidance literature:

Multi-step reaction with 6 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: Me₃SiCl; hexamethyldisilazane / 12 h / 120 °C

6.2: 6.1 g / SnCl₄ / 1,2-dichloro-ethane; acetonitrile / 3 h / 70 °C

With pyridine; hydrogenchloride; chloro-trimethyl-silane; hydrogen bromide; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja048417i

Reference yield:

2-O-methyl-3,4-O-isopropylidene-6-O-(4-toluoyl)-D-psicofuranose (783322-61-2) → 9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N6-benzoyladenine (478487-96-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 12 h / 4 °C

2.1: aq. TFA / 0.42 h / 20 °C

3.1: 5.3 g / pyridine / 3 h / 20 °C

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

5.1: Me₃SiCl; hexamethyldisilazane / 12 h / 120 °C

5.2: 6.1 g / SnCl₄ / 1,2-dichloro-ethane; acetonitrile / 3 h / 70 °C

With pyridine; chloro-trimethyl-silane; hydrogen bromide; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja048417i

upstream raw materials:

N-benzoyladenine

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

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

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]-N⁶-(phenoxyacetyl)adenine

9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)-adenine

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