1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one

Base Information

• Chemical Name: 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one
• CAS No.: 1415236-69-9
• Molecular Formula: C₂₀H₂₄N₈O₉S₂
• Molecular Weight: 584.591
• Mol file: 1415236-69-9.mol

Synonyms:1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one

Chemical Property of 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one

There total 6 articles about 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one 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: 48.0%

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine (552856-39-0) → 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one (1415236-69-9) + 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4)

Guidance literature:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine; With pyridine; dmap; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

With sodium azide; 15-crown-5; In N,N-dimethyl-formamide; at 80 ℃; for 19h; Inert atmosphere;

DOI:10.1021/jo302036h

Reference yield:

1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine (293751-04-9) → 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one (1415236-69-9) + 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonia / methanol / 0 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: sulfuric acid / water; acetone / 3 h / Reflux

4.1: pyridine; dmap; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.2: 19 h / 80 °C / Inert atmosphere

With pyridine; dmap; trifluoromethylsulfonic anhydride; sulfuric acid; ammonia; In methanol; dichloromethane; water; acetone;

DOI:10.1021/jo302036h

Reference yield:

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine (293751-06-1) → 1-(5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-2-deoxy-2-azido-β-D-erythro-pentofuranosyl)-4-azido-5-methylpyrimidin-2(1H)-one (1415236-69-9) + 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl]thymine (552856-41-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: sulfuric acid / water; acetone / 3 h / Reflux

3.1: pyridine; dmap; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / 0 °C / Inert atmosphere

3.2: 19 h / 80 °C / Inert atmosphere

With pyridine; dmap; trifluoromethylsulfonic anhydride; sulfuric acid; In dichloromethane; water; acetone;

DOI:10.1021/jo302036h

upstream raw materials:

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine

1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-erythro-pentofuranosyl)thymine

2,2'-anhydro-1-(3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-β-D-threo-pentofuranosyl)thymine