1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

Base Information

Chemical Name:1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one
CAS No.:1417444-54-2
Molecular Formula:C₃₅H₃₂N₂O₁₀
Molecular Weight:640.646
Hs Code.:

Synonyms:1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

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Chemical Property of 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

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Technology Process of 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

There total 5 articles about 1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one 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:

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 168130-75-4
4,6-dimethyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester

: 1417444-54-2
1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

Guidance literature:: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 4,6-dimethyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 50 ℃; for 1h; Inert atmosphere;

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 3h; Reagent/catalyst; Inert atmosphere;
DOI:10.1016/j.tet.2012.11.017

Reference yield:

: 114762-36-6
2,3,5-tri-O-benzoyl-D-ribofuranosyl fluoride

: 168130-75-4
4,6-dimethyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester

: 1417444-53-1
1-2',3',5'-tri-O-benzoyl-α-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

: 1417444-54-2
1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

Guidance literature:: 2,3,5-tri-O-benzoyl-D-ribofuranosyl fluoride; 4,6-dimethyl-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid ethyl ester; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 50 ℃; for 1h; Inert atmosphere;

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 2h; Overall yield = 90 %; Inert atmosphere;
DOI:10.1016/j.tet.2012.11.017

Reference yield:

: 17994-56-8,64612-96-0,123410-61-7
ethyl 4,6-dimethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

: 1417444-54-2
1-2',3',5'-tri-O-benzoyl-β-D-ribopentofuranosyl-5-(ethoxycarbonyl)-4,6-dimethylpyrimidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyrographite / 5,5-dimethyl-1,3-cyclohexadiene / 140 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 50 °C / Inert atmosphere

2.2: 3 h / 0 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; pyrographite; In 5,5-dimethyl-1,3-cyclohexadiene; acetonitrile;
DOI:10.1016/j.tet.2012.11.017