2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

Base Information

Chemical Name:2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester
CAS No.:208999-76-2
Molecular Formula:C₃₅H₃₀N₂O₁₁
Molecular Weight:654.63
Hs Code.:

Synonyms:2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

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Chemical Property of 2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

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Technology Process of 2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

There total 6 articles about 2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester 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%

: 124-42-5
acetamidine hydrochloride

: 208999-74-0
methyl 2-amino-3-ethoxycarbonyl-4-oxo-4-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2-butenoate

: 208999-76-2
2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

Guidance literature:: With 1,1,3,3-tetramethylguanidine; triethylamine; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1016/S0040-4020(99)00595-5

Reference yield:

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

: 208999-76-2
2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: BF₃*Et₂O / acetonitrile / 0.05 h / 20 °C

2: 69 percent / Zn / tetrahydrofuran / 0.67 h / Heating

3: aq. HCl / tetrahydrofuran / 6 h / 20 °C

4: 85 percent / Ni(acac)2 / CH₂Cl₂ / 96 h / 20 °C

5: 91 percent / Et₃N; tetramethylguanidine / CH₂Cl₂ / 4 h / 0 °C

With hydrogenchloride; bis(acetylacetonate)nickel(II); 1,1,3,3-tetramethylguanidine; boron trifluoride diethyl etherate; triethylamine; zinc; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Substitution / 2: Blaise reaction / 3: Hydrolysis / 4: Addition / 5: Condensation;
DOI:10.1016/S0040-4020(99)00595-5

Reference yield:

: 23316-67-8
2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile

: 208999-76-2
2-methyl-6-(2',3',5'-tri-O-benzoyloxy-β-D-ribofuranosyl)-pyrimidine-4,5-dicarboxylic acid-5-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / Zn / tetrahydrofuran / 0.67 h / Heating

2: aq. HCl / tetrahydrofuran / 6 h / 20 °C

3: 85 percent / Ni(acac)2 / CH₂Cl₂ / 96 h / 20 °C

4: 91 percent / Et₃N; tetramethylguanidine / CH₂Cl₂ / 4 h / 0 °C

With hydrogenchloride; bis(acetylacetonate)nickel(II); 1,1,3,3-tetramethylguanidine; triethylamine; zinc; In tetrahydrofuran; dichloromethane; 1: Blaise reaction / 2: Hydrolysis / 3: Addition / 4: Condensation;
DOI:10.1016/S0040-4020(99)00595-5