(4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

Base Information

• Chemical Name: (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester
• CAS No.: 474081-87-3
• Molecular Formula: C₄₁H₄₄N₂O₇
• Molecular Weight: 676.81
• Mol file: 474081-87-3.mol

Synonyms:(4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

Chemical Property of (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

There total 6 articles about (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid 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: 48.0%

(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methylurea (24751-60-8) + ethyl acetoacetate (141-97-9) + benzaldehyde (100-52-7) → (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (474081-87-3)

Guidance literature:

With boron trifluoride diethyl etherate; acetic acid; copper(l) chloride; In tetrahydrofuran; at 65 ℃; for 24h;

DOI:10.1021/jo0202076

Reference yield:

2,5-anhydro-3,4,6-tri-O-benzyl-aldehydo-D-altrohexofuranose (37699-02-8) → (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (474081-87-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaBH₄ / methanol / 0.17 h / 0 °C

2.1: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 2 h / 100 °C

2.2: 883 mg / NaN₃ / dimethylformamide / 2 h / 100 °C

3.1: H₂ / Pd(OH)2/C / acetic acid / 0.33 h / 20 °C

4.1: 566 mg / ethanol / 1.5 h / Heating

5.1: 48 percent / BF₃*Et₂O; CuCl; glacial acetic acid / tetrahydrofuran / 24 h / 65 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; acetic acid; N,N-dimethyl-formamide; 5.1: Biginelli cyclocondensation;

DOI:10.1021/jo0202076

Reference yield:

(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl alcohol (37699-03-9) → (4RS)-1-[(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl]-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (474081-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 2 h / 100 °C

1.2: 883 mg / NaN₃ / dimethylformamide / 2 h / 100 °C

2.1: H₂ / Pd(OH)2/C / acetic acid / 0.33 h / 20 °C

3.1: 566 mg / ethanol / 1.5 h / Heating

4.1: 48 percent / BF₃*Et₂O; CuCl; glacial acetic acid / tetrahydrofuran / 24 h / 65 °C

With boron trifluoride diethyl etherate; diphenylphosphoranyl azide; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride; palladium dihydroxide; In tetrahydrofuran; ethanol; acetic acid; N,N-dimethyl-formamide; 4.1: Biginelli cyclocondensation;

DOI:10.1021/jo0202076

upstream raw materials:

(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methylurea

ethyl acetoacetate

benzaldehyde

2,5-anhydro-3,4,6-tri-O-benzyl-aldehydo-D-altrohexofuranose