1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

Base Information

Chemical Name:1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose
CAS No.:1233209-82-9
Molecular Formula:C₂₈H₄₆N₂O₃Si₂
Molecular Weight:514.856
Hs Code.:

Synonyms:1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

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Chemical Property of 1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

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Technology Process of 1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

There total 6 articles about 1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose 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: 59.0%

: 1233209-76-1
1β-(2-chloro-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

: 98-80-6
phenylboronic acid

: 1233209-82-9
1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In toluene; at 90 ℃; for 12h; regioselective reaction; Inert atmosphere; Anhydrous reaction;
DOI:10.1002/ejoc.201000164

Reference yield:

: 1233209-66-9
1β-(2,4-dichloropyrimidin-5-yl)-1,2-dideoxy-2,3-didehydro-3-O-(tert-butyldimethylsilyl)-D-ribofuranose

: 1233209-82-9
1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 0.08 h / 0 °C

2: sodium tris(acetoxy)borohydride; acetic acid / acetonitrile / 0.08 h / 0 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

4: iron(III)-acetylacetonate / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene / 12 h / 90 °C / Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III)-acetylacetonate; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Suzuki coupling;
DOI:10.1055/s-0031-1289694

Reference yield:

: 1233209-67-0
1β-(2,4-dichloropyrimidin-5-yl)-1,2,3-trideoxy-3-oxo-D-ribofuranose

: 1233209-82-9
1β-(2-phenyl-4-methylpyrimidin-5-yl)-1,2-dideoxy-3,5-di-O(t-butyldimethylsilyl)-D-ribofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tris(acetoxy)borohydride; acetic acid / acetonitrile / 0.08 h / 0 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

3: iron(III)-acetylacetonate / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene / 12 h / 90 °C / Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III)-acetylacetonate; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Suzuki coupling;
DOI:10.1055/s-0031-1289694