3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine

Base Information

• Chemical Name: 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine
• CAS No.: 851033-74-4
• Molecular Formula: C₅₇H₅₂N₂O₁₃
• Molecular Weight: 973.045
• Mol file: 851033-74-4.mol

Synonyms:3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine

Chemical Property of 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine

There total 3 articles about 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine 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: 63.0%

2,3,4-tri-O-benzyl-1-(phenylsulfinyl)-α-L-rhamnopyranoside (851033-73-3) + 2',3'-O,N3-tribenzoyluridine (55798-09-9) → 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine (851033-74-4)

Guidance literature:

2,3,4-tri-O-benzyl-1-(phenylsulfinyl)-α-L-rhamnopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - -60 ℃; for 0.25h;

2',3'-O,N³-tribenzoyluridine; In dichloromethane; at -60 - -5 ℃; for 1.16667h;

DOI:10.1039/b500418g

Reference yield: 37.0%

2,3,4-tri-O-benzyl-1-(phenylsulfinyl)-α-L-rhamnopyranoside (851033-73-3) + 2',3'-O,N3-tribenzoyluridine (55798-09-9) → 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine (851033-74-4) + 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)-uridine (851033-75-5)

Guidance literature:

With iodine; potassium carbonate; In dichloromethane;

DOI:10.1039/b500418g

Reference yield:

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside (131897-04-6) → 3-N-benzoyl-2',3'-di-O-benzoyl-5'-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-uridine (851033-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / aq. H₂O₂; Ac₂O; silica / CH₂Cl₂

2.1: 2,6-di-tert-butyl-4-methyl pyridine; Tf₂O / CH₂Cl₂ / 0.25 h / -78 - -60 °C

2.2: 63 percent / CH₂Cl₂ / 1.17 h / -60 - -5 °C

With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; dihydrogen peroxide; acetic anhydride; silica gel; In dichloromethane;

DOI:10.1039/b500418g

upstream raw materials:

2,3,4-tri-O-benzyl-1-(phenylsulfinyl)-α-L-rhamnopyranoside

2',3'-O,N³-tribenzoyluridine

phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside