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

Base Information

• Chemical Name: (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5,7-di-tert-butylsilanediyl)-β-oxepinyl]-N⁶-benzoyladenine
• CAS No.: 945534-05-4
• Molecular Formula: C₂₇H₃₅N₅O₄Si
• Molecular Weight: 521.691

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

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

Chemical Property:

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

There total 6 articles about (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5,7-di-tert-butylsilanediyl)-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: 30.0%

N-benzoyladenine (4005-49-6) + 3-acetyl-1,5-anhydro-2-deoxy-1,2-C-methylene-4,6-O-(di-tert-butylsilanediyl)-D-glucal (194938-98-2) → (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5,7-di-tert-butylsilanediyl)-β-oxepinyl]-N6-benzoyladenine (945534-05-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 90 ℃;

DOI:10.1021/ja071336c

Reference yield: 30.0%

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

Guidance literature:

Reference yield:

4,6-O-di(tert-butyl)silanediyl-D-glucal (191593-14-3) → (1R)-1-[(2,3,4-trideoxy-(5S,6R)-5,7-di-tert-butylsilanediyl)-β-oxepinyl]-N6-benzoyladenine (945534-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnEt₂ / hexane

2: pyridine

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

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

DOI:10.1021/ja071336c

upstream raw materials:

N-benzoyladenine

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

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

Downstream raw materials:

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

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