3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

Base Information

Chemical Name:3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine
CAS No.:1300590-87-7
Molecular Formula:C₃₃H₃₁N₃O₉
Molecular Weight:613.624
Hs Code.:

Synonyms:3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

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Chemical Property of 3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

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Technology Process of 3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

There total 12 articles about 3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-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: 91.0%

: 1300590-85-5
3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-5-methyluridine

: 1300590-87-7
3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

Guidance literature:: With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 70 ℃; for 18h; Reflux;

Reference yield:

: 1300589-65-4
3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

: 1300590-87-7
3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; trifluoromethane sulfonyl chloride / dichloromethane / 1 h / 20 °C / Cooling with ice

2.1: sodium hydroxide / tetrahydrofuran; water / 16.5 h / 20 °C

2.2: 20 °C

3.1: pyridine / dichloromethane / 0.67 h / 0 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 20 °C

5.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / Reflux

With pyridine; dmap; trifluoromethane sulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); sodium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo201597e

Reference yield:

: 1300589-63-2
2'-O-acetyl-3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

: 1300590-87-7
3',5'-di-O-benzyl-2'-O-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4'-C-hydroxymethyl-5-methyluridine

Guidance literature:: Multi-step reaction with 6 steps

1.1: methylamine / tetrahydrofuran; water / 0.5 h / 20 °C

2.1: dmap; trifluoromethane sulfonyl chloride / dichloromethane / 1 h / 20 °C / Cooling with ice

3.1: sodium hydroxide / tetrahydrofuran; water / 16.5 h / 20 °C

3.2: 20 °C

4.1: pyridine / dichloromethane / 0.67 h / 0 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 20 °C

6.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / Reflux

With pyridine; dmap; trifluoromethane sulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); methylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo201597e