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

Base Information

• Chemical Name: methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside
• CAS No.: 733050-14-1
• Molecular Formula: C₂₃H₂₆Cl₂O₆
• Molecular Weight: 469.362
• Mol file: 733050-14-1.mol

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

Chemical Property of methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

There total 4 articles about methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside 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: 98.0%

acetic anhydride (108-24-7) + methyl 3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-α-(hydroxymethyl)-α-D-ribofuranoside (733050-13-0) → methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside (733050-14-1)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo0495337

Reference yield:

methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside (108008-66-8) → methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside (733050-14-1)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; Dess-Martin periodane; In tetrahydrofuran; 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) → methyl 2α-acetoxymethyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside (733050-14-1)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/jo0495337

upstream raw materials:

acetic anhydride

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

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

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

Downstream raw materials:

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

5'-O-(dimethoxytrityl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine

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

3',5'-di-O-(tert-butyldimethylsilyl)-2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine