3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine

Base Information

• Chemical Name: 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine
• CAS No.: 212970-81-5
• Molecular Formula: C₃₄H₃₈N₂O₆Si
• Molecular Weight: 598.771
• Mol file: 212970-81-5.mol

Synonyms:3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine

Chemical Property of 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine

There total 4 articles about 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine 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: 94.0%

2'-O-acetyl-3'-O-benzyl-5'-O-t-butyldiphenylsilyl-4'-p-toluenesulfonyloxymethyl-5-methyluridine (212970-75-7) → 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine (212970-81-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1039/b307290h

Reference yield:

3'-O-benzyl-5'-O-t-butyldiphenylsilyl-4'-p-toluenesulfonyloxymethyl-5-methyluridine (212970-78-0) → 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine (212970-81-5)

Guidance literature:

With sodium hexamethyldisilazane; sodium hydrogencarbonate; In tetrahydrofuran; nitrogen; water;

Reference yield:

Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (212970-74-6) → 3'-O-benzyl-5'-O-t-butyldiphenylsilyl-2'-O,4'-C-methylene-5-methyluridine (212970-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / TMSOTf / 1,2-dichloro-ethane / Heating

2: 94 percent / K₂CO₃ / methanol / 20 °C

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In methanol; 1,2-dichloro-ethane;

DOI:10.1039/b307290h

upstream raw materials:

2'-O-acetyl-3'-O-benzyl-5'-O-t-butyldiphenylsilyl-4'-p-toluenesulfonyloxymethyl-5-methyluridine

Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

3'-O-benzyl-5'-O-t-butyldiphenylsilyl-4'-p-toluenesulfonyloxymethyl-5-methyluridine

Downstream raw materials:

(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane