N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide

Base Information

• Chemical Name: N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide
• CAS No.: 139260-81-4
• Molecular Formula: C₃₈H₃₅N₅O₆
• Molecular Weight: 657.726

Synonyms:N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide

Chemical Property of N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide

Chemical Property:

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Technology Process of N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide

There total 4 articles about N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide 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: 97.0%

[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]tetrahydrofuran-3-yl] 4-nitrobenzoate (606141-34-8) → N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide (139260-81-4)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4020(03)00870-6

Reference yield: 82.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N6-benzoyl-9-(2'-deoxy-β-D-threo-pentofuranosyl)adenine (125944-20-9) → N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide (139260-81-4)

Guidance literature:

With pyridine; N-ethyl-N,N-diisopropylamine; for 3h; Ambient temperature;

DOI:10.1002/hlca.19910740840

Reference yield:

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → N-[9-[(2R,4R,5R)-5-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-4-hydroxytetrahydrofuran-2-yl]purin-6-yl]benzamide (139260-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

2: 97 percent / MeONa / methanol / 1.5 h / 0 °C

With sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(03)00870-6

upstream raw materials:

4,4'-dimethoxytrityl chloride

N⁶-benzoyl-9-(2'-deoxy-β-D-threo-pentofuranosyl)adenine

[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]tetrahydrofuran-3-yl] 4-nitrobenzoate

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Downstream raw materials:

N⁶-benzoyl-3',5'-diamino-2',3',5'-trideoxyadenosine

N⁶-benzoyl-3',5'-diazido-2',3',5'-trideoxyadenosine

N⁶-benzoyl-9-(3',5'-di-O-methylsulfonyl-2'-deoxy-β-D-threo-pentofuranosyl)adenine

[(2R,3R,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]tetrahydrofuran-3-yl] methanesulfonate

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