(1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one

Base Information

• Chemical Name: (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one
• CAS No.: 104531-59-1
• Molecular Formula: C₁₆H₁₇N₃O₅
• Molecular Weight: 331.328

Synonyms:(1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one

Chemical Property of (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one

Chemical Property:

Purity/Quality:

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Technology Process of (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one

There total 4 articles about (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one 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: 28.7%

2,2'-anhydro-1-(5'-O-benzoyl-3'-O-methanesulfonyl-β-D-arabinofuranosyl)uracil (56687-59-3) + 4-methoxy-aniline (104-94-9) → (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one (104531-59-1) + 2,3'-<(p-methoxyphenyl)imino>-1-(5'-O-benzoyl-3'-deoxy-β-D-lyxofuranosyl)uracil (104531-58-0)

Guidance literature:

In N,N-dimethyl-formamide; at 125 - 130 ℃; for 65h;

DOI:10.1021/jo00373a014

Reference yield:

2,3'-<(p-methoxyphenyl)imino>-1-(5'-O-benzoyl-3'-deoxy-β-D-lyxofuranosyl)uracil (104531-58-0) → (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one (104531-59-1)

Guidance literature:

With ammonium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/jo00373a014

Reference yield:

2,2'-anhydro-1-(5'-O-benzoyl-3'-O-methanesulfonyl-β-D-arabinofuranosyl)uracil (56687-59-3) → (1R,9R,10S,12S)-12-Hydroxy-10-hydroxymethyl-8-(4-methoxy-phenyl)-11-oxa-2,6,8-triaza-tricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one (104531-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 28.7 percent / dimethylformamide / 65 h / 125 - 130 °C

2: conc. aq. NH₃ / methanol / Ambient temperature

With ammonium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00373a014

upstream raw materials:

2,2'-anhydro-1-(5'-O-benzoyl-3'-O-methanesulfonyl-β-D-arabinofuranosyl)uracil

4-methoxy-aniline

2,3'-<(p-methoxyphenyl)imino>-1-(5'-O-benzoyl-3'-deoxy-β-D-lyxofuranosyl)uracil

Downstream raw materials:

2,3'-<(p-methoxyphenyl)imino>-1-(3'-deoxy-β-D-lyxopyranosyl)uracil

1-(3'-anisidino-3'-deoxy-β-D-lyxofuranosyl)uracil

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