4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine
• CAS No.: 1350887-26-1
• Molecular Formula: C₃₇H₂₈N₆O₇
• Molecular Weight: 668.665
• Mol file: 1350887-26-1.mol

Synonyms:4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine

Chemical Property of 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine

There total 8 articles about 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine 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: 75.0%

N-boc-2-pyrroleboronic acid (135884-31-0) + 4-amino-6-bromo-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine → 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine (1350887-26-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 110 ℃; for 14h;

DOI:10.1016/j.bmc.2011.10.003

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (3080-30-6,6974-32-9,14215-97-5,16162-35-9,20822-87-1,21138-42-1,22249-15-6,22249-17-8,26287-72-9,53403-35-3,53403-36-4,57236-69-8,70832-64-3,99395-04-7,100101-51-7,109668-83-9,120019-54-7) → 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine (1350887-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

1.2: 3.17 h / 20 - 80 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; N,N-dimethyl-formamide / 14 h / 110 °C

With bis-triphenylphosphine-palladium(II) chloride; N,O-bis-(trimethylsilyl)-acetamide; sodium carbonate; In water; N,N-dimethyl-formamide; acetonitrile; 2.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.10.003

Reference yield:

2-amino-5-bromo-1H-pyrrole-3,4-dicarbonitrile (98130-58-6) → 4-amino-6-(1H-pyrrol-2-yl)-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)pyrrolo[2,3-d]pyrimidine (1350887-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,2-dimethoxyethane / 24 h / Reflux

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

2.2: 3.17 h / 20 - 80 °C

3.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; N,N-dimethyl-formamide / 14 h / 110 °C

With bis-triphenylphosphine-palladium(II) chloride; N,O-bis-(trimethylsilyl)-acetamide; sodium carbonate; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.10.003

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

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

L-xylose

4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine