2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

Base Information

Chemical Name:2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine
CAS No.:733050-35-6
Molecular Formula:C₃₃H₃₁Cl₂N₃O₇
Molecular Weight:652.531
Hs Code.:

2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N<sup>4</sup>-benzoylcytidine

Synonyms:2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

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Chemical Property of 2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

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Technology Process of 2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

There total 5 articles about 2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-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: 55.0%

: 26661-13-2
4-N-benzoylcytosine

: 733050-14-1
methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

: Acetic acid (2S,3R,4S,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-(4-chloro-benzyloxy)-5-(4-chloro-benzyloxymethyl)-tetrahydro-furan-3-ylmethyl ester

: 733050-35-6
2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

Guidance literature:: 4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; for 1h; Heating;

methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside; With tin(IV) chloride; In acetonitrile; at 20 - 60 ℃;
DOI:10.1021/jo0495337

Reference yield:

: 108008-66-8
methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside

: 733050-35-6
2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; cyclohexane; 1.1: Dess-Martin oxidation;
DOI:10.1021/jo0495337

Reference yield:

: 733050-11-8
methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside

: 733050-35-6
2'-α-acetoxymethyl-3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-N⁴-benzoylcytidine

Guidance literature:: Multi-step reaction with 4 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

With pyridine; dmap; ammonium sulfate; 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; cyclohexane;
DOI:10.1021/jo0495337