2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

Base Information

• Chemical Name: 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine
• CAS No.: 1300589-63-2
• Molecular Formula: C₄₃H₄₈N₂O₈Si
• Molecular Weight: 748.948
• Mol file: 1300589-63-2.mol

Synonyms:2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

Chemical Property of 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

There total 5 articles about 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-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: 89.0%

acetic anhydride (108-24-7) + thymin (65-71-4,28806-14-6,691841-57-3) + 3,5-di-O-benzyl-4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-α-D-ribofuranose → 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine (1300589-63-2)

Guidance literature:

acetic anhydride; 3,5-di-O-benzyl-4-C-(tert-butyldiphenylsilyloxymethyl)-1,2-O-isopropylidene-α-D-ribofuranose; With sulfuric acid; acetic acid; In ethyl acetate; at 20 ℃; for 3h;

thymin; With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 18h; Reflux;

Reference yield:

C40H46O8Si (1300589-59-6) + thymin (65-71-4,28806-14-6,691841-57-3) → 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine (1300589-63-2)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere; Reflux;

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → 2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine (1300589-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 0 - 20 °C

2.1: sulfuric acid; acetic acid / 5 h / 0 - 20 °C

2.2: 40 °C

2.3: 1 h / 0 - 20 °C

With 1H-imidazole; sulfuric acid; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo201597e

upstream raw materials:

acetic anhydride

thymin

benzyl bromide

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Downstream raw materials:

N₂'-methyl-2'-amino-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-dimethoxytrityl-2'-N,4'-C-oxomethylene thymidine

C₃₃H₃₃N₃O₈

C₃₄H₃₅N₃O₇

C₃₃H₃₃N₃O₇