2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine

Base Information

• Chemical Name: 2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine
• CAS No.: 833486-76-3
• Molecular Formula: C₃₃H₅₃N₅O₅SSi₂
• Molecular Weight: 688.051

Synonyms:2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine

Chemical Property of 2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine

Chemical Property:

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Technology Process of 2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine

There total 2 articles about 2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)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: 75.0%

Phenoxyacetyl chloride (701-99-5) + 2-amino-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine (833486-75-2) → 2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine (833486-76-3)

Guidance literature:

With pyridine; benzotriazol-1-ol; In acetonitrile; for 3h;

DOI:10.1021/jo048298p

Reference yield:

2-amino-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-vinylpurine (188823-57-6) → 2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine (833486-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / acetonitrile; H₂O / 0.33 h / 20 °C

2: 75 percent / 1-hydroxybenzotriazole; pyridine / acetonitrile / 3 h

With pyridine; benzotriazol-1-ol; In water; acetonitrile;

DOI:10.1021/jo048298p

Reference yield: 98.0%

2-[(phenoxyacetyl)amino]-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine (833486-76-3) → 2-[(phenoxyacetyl)amino]-9-(2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine (833486-77-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jo048298p

upstream raw materials:

Phenoxyacetyl chloride

2-amino-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine

2-amino-9-(3',5'-di-O-tert-butyldimethylsilyl-2'-deoxy-β-D-ribofuranosyl)-6-vinylpurine

Downstream raw materials:

2-[(phenoxyacetyl)amino]-9-(2'-deoxy-β-D-ribofuranosyl)-6-(2-methylthioethyl)purine

N-[9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2-methylsulfanyl-ethyl)-9H-purin-2-yl]-2-phenoxy-acetamide

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