3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin

Base Information

• Chemical Name: 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin
• CAS No.: 553664-34-9
• Molecular Formula: C₂₈H₃₀N₂O₉
• Molecular Weight: 538.554
• Mol file: 553664-34-9.mol

Synonyms:3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin

Chemical Property of 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin

There total 7 articles about 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin 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: 88.0%

2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) + 1,3-di-O-acetyl-2-O-(2-methoxyethyl)-5-O-(4-phenylbenzoyl)-β-D-ribose (553664-33-8) → 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin (553664-34-9)

Guidance literature:

With tin(ll) chloride; In acetonitrile; at 65 ℃; for 5h;

DOI:10.1002/hlca.200390013

Reference yield:

Diacetone D-glucose (2595-05-3) → 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin (553664-34-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / potassium hydroxide / dimethylsulfoxide / 7.5 h / 55 °C

2.1: 87 percent / AcOH / H₂O / 2 h / 40 °C

3.1: 70 percent / c-C₅H₅N / CH₂Cl₂ / 5 h / 20 °C

4.1: 100 percent / Amberlit IR-120 / methanol; tetrahydrofuran; H₂O / 6.5 h / 60 °C

5.1: NaIO₄ / ethanol; H₂O / 24 h / 20 °C

5.2: HCl / acetone / 24 h / 20 °C

5.3: 82 percent / c-C₅H₅N / 4 h / 40 °C

6.1: 88 percent / tin(II) chloride / acetonitrile / 5 h / 65 °C

With pyridine; potassium hydroxide; sodium periodate; Amberlit IR-120; acetic acid; tin(ll) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/hlca.200390013

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3'-O-Acetyl-2'-O-(2-methoxyethyl)-5-methyl-5'-O-(4-phenylbenzoyl)uridin (553664-34-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trifluoroacetic anhydride; triethylamine; DMSO / CH₂Cl₂ / -65 - 20 °C

1.2: 82 percent / sodium borohydride / methanol / 1 h / 0 °C

2.1: 95 percent / potassium hydroxide / dimethylsulfoxide / 7.5 h / 55 °C

3.1: 87 percent / AcOH / H₂O / 2 h / 40 °C

4.1: 70 percent / c-C₅H₅N / CH₂Cl₂ / 5 h / 20 °C

5.1: 100 percent / Amberlit IR-120 / methanol; tetrahydrofuran; H₂O / 6.5 h / 60 °C

6.1: NaIO₄ / ethanol; H₂O / 24 h / 20 °C

6.2: HCl / acetone / 24 h / 20 °C

6.3: 82 percent / c-C₅H₅N / 4 h / 40 °C

7.1: 88 percent / tin(II) chloride / acetonitrile / 5 h / 65 °C

With pyridine; potassium hydroxide; sodium periodate; Amberlit IR-120; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; tin(ll) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/hlca.200390013

upstream raw materials:

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

1,3-di-O-acetyl-2-O-(2-methoxyethyl)-5-O-(4-phenylbenzoyl)-β-D-ribose

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

2'-O-(2-methoxyethyl)-5-methyluridine

Refernces