1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil

Base Information

• Chemical Name: 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil
• CAS No.: 685137-21-7
• Molecular Formula: C₂₆H₂₆FN₃O₈S
• Molecular Weight: 559.572
• Mol file: 685137-21-7.mol

Synonyms:1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil

Chemical Property of 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil

There total 2 articles about 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil 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: 83.0%

5-fluorouracil (51-21-8) + N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + 3,5-di-O-benzyl-1,2-O-thiocarbonyl-α-D-ribo-furanose (581795-68-8) → 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil (685137-21-7)

Guidance literature:

5-fluorouracil; N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 0.25h;

3,5-di-O-benzyl-1,2-O-thiocarbonyl-α-D-ribo-furanose; With N-iodo-succinimide; In acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tetasy.2003.12.037

Reference yield:

(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol (561055-45-6) → 1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil (685137-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / CH₂Cl₂ / 0.5 h / 20 °C

2.1: acetonitrile / 0.25 h

2.2: 83 percent / NIS / acetonitrile / 0.17 h / 20 °C

In dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2003.12.037

Reference yield: 90.0%

1-(2'-O-acetamidomercaptocarbonyl-3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil (685137-21-7) → 1-(3',5'-di-O-benzyl-β-D-ribo-furanosyl)-5-fluorouracil

Guidance literature:

With potassium hydroxide; In water; at 50 ℃;

DOI:10.1016/j.tetasy.2003.12.037

upstream raw materials:

5-fluorouracil

N,O-bis-(trimethylsilyl)-acetamide

3,5-di-O-benzyl-1,2-O-thiocarbonyl-α-D-ribo-furanose

(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol