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

Base Information

• Chemical Name: (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepinyl]-N⁶-benzoyladenine
• CAS No.: 945534-07-6
• Molecular Formula: C₁₉H₁₉N₅O₄
• Molecular Weight: 381.391

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

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

Chemical Property:

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

There total 6 articles about (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepinyl]-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: 61.0%

(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5,7-di-tert-butylsilanediyl)-β-oxepinyl]-N6-benzoyladenine (945534-05-4) → (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepinyl]-N6-benzoyladenine (945534-07-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ja071336c

Reference yield:

4,6-O-di(tert-butyl)silanediyl-D-glucal (191593-14-3) → (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5-hydroxy-6-hydroxymethyl)-β-oxepinyl]-N6-benzoyladenine (945534-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: ZnEt₂ / hexane

2: pyridine

3: 30 percent / TMSOTf / acetonitrile / 90 °C

4: 61 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; diethylzinc; In tetrahydrofuran; hexane; acetonitrile; 1: Simmons-Smiths reaction / 3: Vorbrueggen glycosylation;

DOI:10.1021/ja071336c

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-oxepinyl]-N6-benzoyladenine (945534-07-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

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

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

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile; 2: Vorbrueggen glycosylation;

DOI:10.1021/ja071336c

upstream raw materials:

(1R)-1-[(2,3,4-trideoxy-(5S,6R)-5,7-di-tert-butylsilanediyl)-β-oxepinyl]-N⁶-benzoyladenine

4,6-O-di(tert-butyl)silanediyl-D-glucal

(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-6-hydroxymethyl)-β-oxepanyl]-N⁶-benzoyladenine

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

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