Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester

Base Information

• Chemical Name: Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester
• CAS No.: 1053315-55-1
• Molecular Formula: C₃₇H₃₈N₆O₇
• Molecular Weight: 678.745
• Mol file: 1053315-55-1.mol

Synonyms:Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester

Chemical Property of Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester

There total 24 articles about Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl 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:

1,2,4-Triazole (288-88-0) + Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester → Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester (1053315-55-1)

Guidance literature:

With triethylamine; trichlorophosphate; In acetonitrile;

DOI:10.1039/b208864a

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester (1053315-55-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: aq. H₂SO₄ / acetic acid / 18 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / 0 °C

3.2: trimethylsilyl triflate / acetonitrile / 2 h / 65 °C

4.1: 84 percent / methanolic ammonia / methanol / 0 - 20 °C

5.1: pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: 98 percent / DBU / dimethylformamide / 20 °C

7.1: 80 percent / aq. HCl / CH₂Cl₂ / 5 h / 80 °C

8.1: pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 73 h / 0 - 7 °C

8.2: 25 percent / NaN₃ / dimethylformamide / 18.5 h / 20 - 80 °C

9.1: aq LiOH / tetrahydrofuran / 9 h

10.1: 2.91 g / pyridine / 0 - 20 °C

11.1: 93 percent / aq. NaOH; PMe₃ / tetrahydrofuran / 8 h / 20 °C

12.1: 90 percent / formic acid / 1 h / 80 °C

13.1: dimethylformamide / 7 h / 100 °C

14.1: 2.42 g / NaOMe / dimethylformamide / 1 h / 20 °C

15.1: 97 percent / H₂ / Pd(OH)2/C / acetic acid / 8 h

16.1: 92 percent / pyridine / 9 h / 20 °C

17.1: pyridine / 24 h / 20 °C

18.1: Et₃N; POCl₃ / acetonitrile

With pyridine; hydrogenchloride; lithium hydroxide; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; hydrogen; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic anhydride; trichlorophosphate; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; methanol; formic acid; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b208864a

Reference yield:

1-(3-O-benzyl-5-O-benzoyl-4-C-benzoyloxymethyl-β-D-threo-pentofuranosyl)thymine (552856-59-4) → Acetic acid (1R,3R,4R,7S)-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-methyl-3-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]hept-7-yl ester (1053315-55-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 73 h / 0 - 7 °C

1.2: 25 percent / NaN₃ / dimethylformamide / 18.5 h / 20 - 80 °C

2.1: aq LiOH / tetrahydrofuran / 9 h

3.1: 2.91 g / pyridine / 0 - 20 °C

4.1: 93 percent / aq. NaOH; PMe₃ / tetrahydrofuran / 8 h / 20 °C

5.1: 90 percent / formic acid / 1 h / 80 °C

6.1: dimethylformamide / 7 h / 100 °C

7.1: 2.42 g / NaOMe / dimethylformamide / 1 h / 20 °C

8.1: 97 percent / H₂ / Pd(OH)2/C / acetic acid / 8 h

9.1: 92 percent / pyridine / 9 h / 20 °C

10.1: pyridine / 24 h / 20 °C

11.1: Et₃N; POCl₃ / acetonitrile

With pyridine; lithium hydroxide; sodium hydroxide; hydrogen; sodium methylate; triethylamine; trifluoroacetic anhydride; trichlorophosphate; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; formic acid; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b208864a

upstream raw materials:

1,2,4-Triazole

5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

1,2-di-O-acetyl-5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-D-erythro-pentofuranose

2,2-anhydro-1-(5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-β-D-threo-pentofuranosyl)thymine

Downstream raw materials:

(1R,3R,4R,7S)-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methyl-3-(4-benzoyl-5-methylcytosin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-N-methyl-3-(4-amino-5-methyl-cytosine-1-yl)-2-oxa-5-azabicyclo[2:2:1]heptane