2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile

Base Information

• Chemical Name: 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile
• CAS No.: 110099-70-2
• Molecular Formula: C₃₅H₃₃BrN₄O₅
• Molecular Weight: 669.575

Synonyms:2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile

Chemical Property of 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile

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Technology Process of 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile

There total 2 articles about 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile 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: 79.0%

2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride (4060-34-8) + 2-bromo-5-(ethoxymethyleneamino)pyrrole-3,4-dicarbonitrile (110089-43-5) → 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile (110099-70-2)

Guidance literature:

With sodium hydride; In acetonitrile;

DOI:10.1016/S0040-4020(01)96068-5

Reference yield:

2-amino-5-bromo-1H-pyrrole-3,4-dicarbonitrile (98130-58-6) → 2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile (110099-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / acetonitrile / 3 h / Heating

2: 79 percent / NaH / acetonitrile

With sodium hydride; In acetonitrile;

DOI:10.1016/S0040-4020(01)96068-5

Reference yield: 89.0%

2-ethoxymethyleneamino-5-bromo-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-3,4-dicarbonitrile (110099-70-2) → 4-amino-6-bromo-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile (110089-54-8)

Guidance literature:

With ammonia; In methanol; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96068-5

upstream raw materials:

2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride

2-bromo-5-(ethoxymethyleneamino)pyrrole-3,4-dicarbonitrile

2-amino-5-bromo-1H-pyrrole-3,4-dicarbonitrile

Downstream raw materials:

4-amino-6-bromo-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile

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