1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil

Base Information

• Chemical Name: 1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil
• CAS No.: 361344-44-7
• Molecular Formula: C₄₅H₄₄N₂O₈
• Molecular Weight: 740.853
• Mol file: 361344-44-7.mol

Synonyms:1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil

Chemical Property of 1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil

There total 1 articles about 1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil 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: 85.0%

benzyl bromide (100-39-0) + 1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil (175355-17-6) → 1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil (361344-44-7)

Guidance literature:

benzyl bromide; 1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 8h;

benzyl bromide; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 15h; Further stages.;

DOI:10.1021/jo015664l

Reference yield: 94.0%

1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil (361344-44-7) → 1-[1',4'-di-O-benzyl-3'-deoxy-β-D-psicofuranosyl]uracil (361344-45-8)

Guidance literature:

With acetic acid; In dichloromethane; for 1.5h;

DOI:10.1021/jo015664l

Reference yield:

1-[1',4'-di-O-benzyl-3'-deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil (361344-44-7) → (1S,5R,6S)-6-benzyloxy-5-benzyloxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane (361344-50-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / aq. AcOH / CH₂Cl₂ / 1.5 h

2: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h

3: 1.27 percent / aq. NaOH / dioxane; H₂O / 22 h

4: pyridine / 1.33 h / 0 °C

5: 252 mg / H₂ / Pd(OH)2C / CH₂Cl₂; ethanol / 7 h

6: 64 percent / aq. NaOH / dioxane / 22 h / 90 °C

7: dimethylformamide / 36 h / 120 °C

With pyridine; sodium hydroxide; hydrogen; Dess-Martin periodane; acetic acid; palladium hydroxide - carbon; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo015664l

upstream raw materials:

benzyl bromide

1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil

Downstream raw materials:

1-[1',4'-di-O-benzyl-3'-deoxy-β-D-psicofuranosyl]uracil

(1S,5S,6S)-6-benzyloxy-5-hydroxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

(1S,5R,6S)-6-benzyloxy-5-methanesulfonyloxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

(1S,5R,6S)-6-benzyloxy-5-benzyloxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane