benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Base Information

• Chemical Name: benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester
• CAS No.: 664329-46-8
• Molecular Formula: C₃₃H₄₀N₄O₁₁S₂
• Molecular Weight: 732.833
• Mol file: 664329-46-8.mol

Synonyms:benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Chemical Property of benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

There total 13 articles about benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-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: 99.0%

tiolacetic acid (507-09-5) + Benzoic acid 2-[(2R,3S,5R)-3-{2-[(2R,3R,5R)-3-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (664329-45-7) → benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (664329-46-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 1.5h;

DOI:10.1002/hlca.200390244

Reference yield:

1-[3'-[[[(tert-butyl)diphenylsilyl]oxy]methyl]-2',3',5'-trideoxy-β-D-erythro-hexofuranosyl]thymine (651020-33-6) → benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (664329-46-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / pyridine / CH₂Cl₂ / 3 h / 20 °C

2: 82 percent / Cs₂CO₃ / dimethylformamide / 4 h / 45 °C

3: oxone; NaOAc / methanol; tetrahydrofuran; H₂O

4: 350 mg / oxone; NaOAc / methanol; tetrahydrofuran; H₂O / 2 h

5: 99 percent / ZnCl₂*Et₂O / CH₂Cl₂

6: 71 percent / pyridine; N,N-dimethylpyridin-4-amine / 5 h / 20 °C

7: 91 percent / Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

8: 99 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 1.5 h

With pyridine; dmap; Oxone; zinc chloride diethyl ether; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium acetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 8: Mitsunobu reaction;

DOI:10.1002/hlca.200390244

Reference yield:

benzoyl chloride (98-88-4) → benzoic acid 2-[3-{2-[3-acetylsulfanylmethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester (664329-46-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / pyridine; N,N-dimethylpyridin-4-amine / 5 h / 20 °C

2: 91 percent / Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

3: 99 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 1.5 h

With pyridine; dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; 3: Mitsunobu reaction;

DOI:10.1002/hlca.200390244

upstream raw materials:

tiolacetic acid

Benzoic acid 2-[(2R,3S,5R)-3-{2-[(2R,3R,5R)-3-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

benzoyl chloride

1-[6'-O-benzoyl-2',3',5'-trideoxy-3'-(mercaptomethyl)-β-D-erythro-hexofuranosyl]thymine

Downstream raw materials:

C₅₂H₅₆N₄O₁₂S₂

C₄₅H₅₂N₄O₁₁S₂

C₄₅H₅₁BrN₄O₁₀S₂

Benzoic acid 2-[(2R,3S,5R)-3-{2-[(2R,3S,5R)-3-mercaptomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonylmethyl}-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester