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

Base Information

• Chemical Name: methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside
• CAS No.: 733050-11-8
• Molecular Formula: C₂₀H₂₀Cl₂O₅
• Molecular Weight: 411.282
• Mol file: 733050-11-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-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: 97.0%

methyl 3,5-di-O-(4-chlorobenzyl)-α-D-ribofuranoside (108008-66-8) → methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside (733050-11-8)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 80 ℃; for 3h;

DOI:10.1002/ejoc.201001448

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside (733050-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / 72 h / 20 °C

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

2.2: 0 - 20 °C

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

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 80 °C

With hydrogenchloride; tin(IV) chloride; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/ejoc.201001448

Reference yield:

methyl α-D-ribofuranoside (52485-92-4) → methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside (733050-11-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride; tin(IV) chloride / N,N-dimethyl-formamide / 4 h / 0 - 30 °C

2: tin(IV) chloride / dichloromethane / 24 h / 0 - 30 °C

3: trichloroisocyanuric acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 18 h / 0 - 30 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; tin(IV) chloride; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2021.113852

upstream raw materials:

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

methyl ribofuranoside

D-Ribose

methyl α-D-ribofuranoside

Downstream raw materials:

methyl-3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-methylene-β-D-ribofuranoside

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

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

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