(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N⁶-benzoyladenine

Base Information

• Chemical Name: (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N⁶-benzoyladenine
• CAS No.: 945534-09-8
• Molecular Formula: C₁₉H₂₁N₅O₄
• Molecular Weight: 383.407

Synonyms:(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N⁶-benzoyladenine

Chemical Property of (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N⁶-benzoyladenine

Chemical Property:

Purity/Quality:

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Technology Process of (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N⁶-benzoyladenine

There total 4 articles about (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-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: 99.0%

(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepinyl]-N6-benzoyladenine (945534-07-6) → (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N6-benzoyladenine (945534-09-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 22 ℃; for 4h; under 760.051 Torr;

DOI:10.1021/ja071336c

Reference yield: 99.0%

→ (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N6-benzoyladenine (945534-09-8)

Guidance literature:

Reference yield:

(1aS,2aR,6aS,7R,7aS)-5,5-Di-tert-butyl-hexahydro-2,4,6-trioxa-5-sila-cyclopropa[b]naphthalen-7-ol (194938-97-1) → (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepanyl]-N6-benzoyladenine (945534-09-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: 30 percent / TMSOTf / acetonitrile / 90 °C

3: 61 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

4: 99 percent / H₂ / Pd/C / methanol / 4 h / 22 °C / 760.05 Torr

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile; 2: Vorbrueggen glycosylation;

DOI:10.1021/ja071336c

upstream raw materials:

(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepinyl]-N⁶-benzoyladenine

(1aS,2aR,6aS,7R,7aS)-5,5-Di-tert-butyl-hexahydro-2,4,6-trioxa-5-sila-cyclopropa[b]naphthalen-7-ol

3-acetyl-1,5-anhydro-2-deoxy-1,2-C-methylene-4,6-O-(di-tert-butylsilanediyl)-D-glucal

Downstream raw materials:

(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-7-[4-(methoxyphenyl)diphenyl])-β-oxepanyl]-N6-benzoyladenine

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