3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

Base Information

Chemical Name:3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine
CAS No.:1300590-46-8
Molecular Formula:C₄₃H₄₇F₃N₂O₉SSi
Molecular Weight:853.001
Hs Code.:

Synonyms:3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

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Chemical Property of 3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

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Technology Process of 3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

There total 9 articles about 3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine 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%

: 358-23-6
trifluoromethylsulfonic anhydride

: 1300590-44-6
3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methylarabinouridine

: 1300590-46-8
3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

Reference yield:

: 1300590-32-2
3,5-di-O-benzyl-4-C-(2-t-butyldiphenylsilyloxyethyl)1,2-di-O-acetyl-α-D-erythropentofuranose

: 1300590-46-8
3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / Inert atmosphere; Reflux

1.2: 3.5 h / 0 °C / Reflux; Inert atmosphere

2.1: potassium carbonate / methanol / 1 h / 20 °C

3.1: triethylamine; trifluoromethane sulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

4.1: sodium hydroxide; water / ethanol / 12 h / 20 °C

5.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; trifluoromethane sulfonyl chloride; water; potassium carbonate; triethylamine; sodium hydroxide; In methanol; ethanol; dichloromethane; acetonitrile;

Reference yield:

: 287737-62-6
2-((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol

: 1300590-46-8
3’,5’-di-O-benzyl-4’-(2-tert-butyldiphenylsiloxyethyl)-5-methyl-2’-O-(trifluoromethanesulfonyl)arabinouridine

Guidance literature:: Multi-step reaction with 7 steps

1.1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: acetic anhydride; sulfuric acid; acetic acid / 2 h / 20 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / Inert atmosphere; Reflux

3.2: 3.5 h / 0 °C / Reflux; Inert atmosphere

4.1: potassium carbonate / methanol / 1 h / 20 °C

5.1: triethylamine; trifluoromethane sulfonyl chloride / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

6.1: sodium hydroxide; water / ethanol / 12 h / 20 °C

7.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trifluoromethane sulfonyl chloride; sulfuric acid; water; acetic anhydride; potassium carbonate; acetic acid; triethylamine; sodium hydroxide; In methanol; ethanol; dichloromethane; acetonitrile;