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

Base Information

• Chemical Name: 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
• CAS No.: 291758-30-0
• Molecular Formula: C₃₁H₄₅ClN₄O₇SSi₂
• Molecular Weight: 709.411
• Mol file: 291758-30-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 65.0%

6-chloropurine (87-42-3) + 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-7-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-thio-β-D-ribofuranosyl]-9H-purine + 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In 1,2-dichloro-ethane; acetonitrile; at 83 ℃; for 24h;

DOI:10.1021/ja000541o

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-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) → (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrothiophene-3,4-diol (2500-80-3,4303-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / TBAF; AcOH / tetrahydrofuran / 0.17 h / 20 °C

2: 83 percent / NH₃ / ethanol / 24 h / 100 °C

With tetrabutyl ammonium fluoride; ammonia; acetic acid; In tetrahydrofuran; ethanol; 1: Desilylation / 2: Amminolysis; Substitution;

DOI:10.1021/ja000541o

upstream raw materials:

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:

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

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