methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine

Base Information

• Chemical Name: methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine
• CAS No.: 1276113-04-2
• Molecular Formula: C₃₉H₃₃Cl₂N₅O₆
• Molecular Weight: 738.627
• Mol file: 1276113-04-2.mol

Synonyms:methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine

Chemical Property of methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine

There total 9 articles about methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine 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:

methyl 2-α-(benzoyloxymethyl)-3,5-di-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside (1276113-06-4) + N-Benzoyl-N,9-bis(trimethylsilyl)adenin (18055-47-5) → methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine (1276113-04-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 80 ℃; for 5h;

DOI:10.1002/ejoc.201001448

Reference yield:

methyl 2,3,5-tri-O-(4-chlorobenzyl)-α-D-ribofuranoside → methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine (1276113-04-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tin(IV) chloride / dichloromethane / 6 h / 0 °C

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 80 °C

3.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C

3.2: -78 - 20 °C

4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 20 - 40 °C

4.2: 3 h / 20 - 80 °C

5.1: pyridine / 5 h / 20 °C

6.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h / 80 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sec.-butyllithium; tin(IV) chloride; 9-bora-bicyclo[3.3.1]nonane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; cyclohexane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/ejoc.201001448

Reference yield:

methyl ribofuranoside (1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7) → methyl N6-benzoyl-2'-α-(benzoyloxymethyl)-3',5'-di-O-(4-chlorobenzyl)-2'-deoxyadenosine (1276113-04-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / dimethyl sulfoxide / 5.75 h / 20 - 60 °C

1.2: 0 - 20 °C

2.1: tin(IV) chloride / dichloromethane / 6 h / 0 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 80 °C

4.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C

4.2: -78 - 20 °C

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 20 - 40 °C

5.2: 3 h / 20 - 80 °C

6.1: pyridine / 5 h / 20 °C

7.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h / 80 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sec.-butyllithium; tin(IV) chloride; sodium hydride; 9-bora-bicyclo[3.3.1]nonane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/ejoc.201001448

upstream raw materials:

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

N-Benzoyl-N,9-bis(trimethylsilyl)adenin

methyl ribofuranoside

D-Ribose

Downstream raw materials:

methyl 3',5'-di-O-(4-chlorobenzyl)-2'-deoxy-2'-(hydroxymethyl)adenosine