6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine

Base Information

• Chemical Name: 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine
• CAS No.: 291758-31-1
• Molecular Formula: C₁₉H₁₉ClN₄O₆S
• Molecular Weight: 466.902

Synonyms:6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine

Chemical Property of 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine

Chemical Property:

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Technology Process of 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine

There total 3 articles about 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine 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: 99.0%

6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]-9H-purine (291758-30-0) → 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine (291758-31-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1021/ja000541o

Reference yield:

6-chloropurine (87-42-3) → 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine (291758-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 9 percent / Et₃N; TMSOTf / toluene; CH₂Cl₂ / 0.08 h / 20 °C

2: 99 percent / TBAF; AcOH / tetrahydrofuran / 0.17 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Pummerer reaction / 2: Desilylation;

DOI:10.1021/ja000541o

Reference yield:

1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol (869347-03-5) → 6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-4-thio-β-D-ribofuranosyl]-9H-purine (291758-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 9 percent / Et₃N; TMSOTf / toluene; CH₂Cl₂ / 0.08 h / 20 °C

2: 99 percent / TBAF; AcOH / tetrahydrofuran / 0.17 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Pummerer reaction / 2: Desilylation;

DOI:10.1021/ja000541o

upstream raw materials:

6-chloro-9-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]-9H-purine

6-chloropurine

1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol

Downstream raw materials:

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrothiophene-3,4-diol

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