N⁶-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine

Base Information

• Chemical Name: N⁶-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine
• CAS No.: 406479-35-4
• Molecular Formula: C₃₄H₃₅N₅O₄
• Molecular Weight: 577.683

Synonyms:N⁶-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine

Chemical Property of N⁶-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine

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Technology Process of N⁶-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine

There total 2 articles about N⁶-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine 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: 50.0%

l-amphetamine (156-34-3,17108-96-2,96332-84-2) + 6-chloro-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-D-psicofuranosyl)purine (406479-32-1) → N6-[(1R)-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-α-D-psicofuranosyl)adenine + N6-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine (406479-35-4)

Guidance literature:

In ethanol; for 6h; Heating;

DOI:10.1021/jm0102755

Reference yield:

2,3-O-benzylidene-D-ribono-1,4-lactone → N6-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine (406479-35-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 49 percent / NaH / tetrahydrofuran / 20 °C

2: diethyl ether / 0.75 h / -78 °C

3: DMAP; pyridine / 48 h / 20 °C

4: 85 percent / EtAlCl₂ / acetonitrile; toluene / 2 h / 20 °C

5: 50 percent / ethanol / 6 h / Heating

With pyridine; dmap; ethylaluminum dichloride; sodium hydride; In tetrahydrofuran; diethyl ether; ethanol; toluene; acetonitrile;

DOI:10.1021/jm0102755

Reference yield: 52.0%

N6-[(1R)-1-methyl-2-phenylethyl]-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-β-D-psicofuranosyl)adenine (406479-35-4) → N6-[(1R)-1-methyl-2-phenylethyl]-9H-(1-deoxy-β-D-psicofuranosyl)adenine

Guidance literature:

With ammonium formate; 10percent Pd/C; In methanol; for 2.5h; Heating;

DOI:10.1021/jm0102755

upstream raw materials:

l-amphetamine

6-chloro-9H-(6-O-benzyl-3,4-O-benzylidene-1-deoxy-D-psicofuranosyl)purine

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