1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

Base Information

• Chemical Name: 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine
• CAS No.: 644961-34-2
• Molecular Formula: C₃₇H₃₆N₂O₁₃
• Molecular Weight: 716.698

Synonyms:1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

Chemical Property of 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

Chemical Property:

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Technology Process of 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

There total 3 articles about 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine 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%

1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine (644961-33-1) → 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine (644961-34-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1081/NCN-120022028

Reference yield:

5'-O-tert-butyldiphenylsilylthymidine (101527-40-6) → 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine (644961-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / SnCl₄ / 1,2-dichloro-ethane / 1.5 h / 0 °C

2: 75 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 20 °C

With tetrabutyl ammonium fluoride; tin(IV) chloride; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1081/NCN-120022028

Reference yield:

1,2,3-tri-O-benzoyl-5-O-(phenoxyacetyl)-D-ribofuranose → 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine (644961-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / SnCl₄ / 1,2-dichloro-ethane / 1.5 h / 0 °C

2: 75 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 20 °C

With tetrabutyl ammonium fluoride; tin(IV) chloride; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1081/NCN-120022028

upstream raw materials:

1-[5-O-tert-butyldiphenylsilyl-3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

5'-O-tert-butyldiphenylsilylthymidine

Downstream raw materials:

1-[5-O-(4'-monomethoxytrityl)-3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

1-[5-O-(4'-monomethoxytrityl)-3-O-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine

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