2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine

Base Information

• Chemical Name: 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine
• CAS No.: 733050-19-6
• Molecular Formula: C₃₈H₃₁N₃O₉
• Molecular Weight: 673.679
• Mol file: 733050-19-6.mol

Synonyms:2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine

Chemical Property of 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine

There total 8 articles about 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N⁴-benzoylcytidine 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: 57.0%

benzoyl chloride (98-88-4) + 2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine (733050-18-5) → 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N4-benzoylcytidine (733050-19-6)

Guidance literature:

2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine; With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 7h;

benzoyl chloride; With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0495337

Reference yield:

methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside (108008-66-8) → 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N4-benzoylcytidine (733050-19-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

2.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

3.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

4.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

5.1: TMS₂NH; (NH₄)2SO₄ / 1 h / Heating

5.2: 55 percent / SnCl₄ / acetonitrile / 20 - 60 °C

6.1: 83 percent / NH₃ / methanol / 48 h / 0 - 4 °C

7.1: 93 percent / pyridine / 24 h / 20 °C

8.1: H₂ / Pd/C / methanol / 7 h / 20 °C

8.2: 57 percent / DMAP; Et₃N / dimethylformamide / 20 °C

With pyridine; dmap; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; hydrogen; sec.-butyllithium; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; 1.1: Dess-Martin oxidation;

DOI:10.1021/jo0495337

Reference yield:

methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside (733050-11-8) → 2'-α-(benzoyloxymethyl)-3',5'-di-O-(benzoyl)-2'-deoxy-N4-benzoylcytidine (733050-19-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: s-BuLi / cyclohexane; tetrahydrofuran / 1 h / -78 °C

1.2: 63 percent / cyclohexane; tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 h / 20 °C

2.2: 84 percent / NaBO₃; H₂O / tetrahydrofuran / 3 h / 20 °C

3.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

4.1: TMS₂NH; (NH₄)2SO₄ / 1 h / Heating

4.2: 55 percent / SnCl₄ / acetonitrile / 20 - 60 °C

5.1: 83 percent / NH₃ / methanol / 48 h / 0 - 4 °C

6.1: 93 percent / pyridine / 24 h / 20 °C

7.1: H₂ / Pd/C / methanol / 7 h / 20 °C

7.2: 57 percent / DMAP; Et₃N / dimethylformamide / 20 °C

With pyridine; dmap; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; ammonia; hydrogen; sec.-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; cyclohexane;

DOI:10.1021/jo0495337

upstream raw materials:

benzoyl chloride

2'-α-(tert-butyldimethylsiloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxycytidine

methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside

methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside