3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE

Base Information

• Chemical Name: 3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE
• CAS No.: 97974-93-1
• Molecular Formula: C27H28 N2 O8
• Molecular Weight: 508.52
• Mol file: 97974-93-1.mol

Synonyms:3’,5’-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2’-DEOXYURIDINE

Chemical Property of 3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE

Chemical Property:

• PSA: 136.92000
• LogP: 2.05830

Purity/Quality:

97% ^*data from raw suppliers

3'',5''-Di-O-(p-toluoyl)-5-(2-hydroxyethyl)-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3'',5''-Di-O-(p-toluoyl)-5-(2-hydroxyethyl)-2''-deoxyuridine can be used as reactant/reagent in preparation of hydroxyl-group-functionalized nucleoside analogs using efficient orthogonal protecting strategy and DNA duplex stability of derived oligodeoxynucleotides.

Technology Process of 3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE

There total 8 articles about 3',5'-DI-O-(P-TOLUOYL)-5-(2-HYDROXYETHYL)-2'-DEOXYURIDINE 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: 90.0%

1-(3,5-Di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2-hydroxyethyl)-4-methoxypyrimidin-2-one (259737-45-6) → 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-(2-hydroxyethyl)-1H,3H-pyrimidine-2,4-dione (97974-93-1)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; for 0.0166667h;

DOI:10.1055/s-1999-3641

Reference yield:

2,4-dimethoxy-5-(2-hydroxyethyl)pyrimidine (108008-56-6) → 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-(2-hydroxyethyl)-1H,3H-pyrimidine-2,4-dione (97974-93-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / pyridine / 1 h / 20 °C

2.1: 20 h / 20 °C

3.1: 100 percent / NaOMe / methanol / 1 h / 20 °C

4.1: BSA / CHCl₃ / 0.17 h / 20 °C

4.2: TMSOTf / CHCl₃ / 1 h / 20 °C

5.1: 90 percent / Me₃SiCl; NaI / acetonitrile / 0.02 h

With pyridine; benzenesulfonamide; chloro-trimethyl-silane; sodium methylate; sodium iodide; In methanol; chloroform; acetonitrile; 1.1: Acetylation / 2.1: Acetylation / 3.1: Deacetylation / 4.1: Substitution / 4.2: Substitution / 5.1: Demethylation;

DOI:10.1055/s-1999-3641

Reference yield:

5-(2-Acetoxyethyl)-2,4-dimethoxypyrimidine (259737-41-2) → 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-(2-hydroxyethyl)-1H,3H-pyrimidine-2,4-dione (97974-93-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 20 h / 20 °C

2.1: 100 percent / NaOMe / methanol / 1 h / 20 °C

3.1: BSA / CHCl₃ / 0.17 h / 20 °C

3.2: TMSOTf / CHCl₃ / 1 h / 20 °C

4.1: 90 percent / Me₃SiCl; NaI / acetonitrile / 0.02 h

With benzenesulfonamide; chloro-trimethyl-silane; sodium methylate; sodium iodide; In methanol; chloroform; acetonitrile; 1.1: Acetylation / 2.1: Deacetylation / 3.1: Substitution / 3.2: Substitution / 4.1: Demethylation;

DOI:10.1055/s-1999-3641

upstream raw materials:

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride

5-(2-hydroxyethyl)-uracil

1-(3,5-Di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-(2-hydroxyethyl)-4-methoxypyrimidin-2-one

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Downstream raw materials:

5-(2-bromoethyl)uracil

1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-(2-tert-butyldiphenylsilyloxyethyl)-1H,3H-pyrimidine-2,4-dione