Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 156592-87-9
• Molecular Formula: C₂₈H₂₂N₄O₉S₄
• Molecular Weight: 686.768
• Mol file: 156592-87-9.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester

There total 8 articles about Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl 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:

2-nitrobenzenesulfenyl chloride (7669-54-7) + Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(4-methoxy-benzylsulfanyl)-tetrahydro-furan-2-ylmethyl ester → Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester (156592-87-9)

Guidance literature:

With acetic acid; In dichloromethane; at 0 ℃; for 4h; Yield given;

DOI:10.1039/c39940000133

Reference yield:

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione (110524-37-3) → Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester (156592-87-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / N,N-dimethyl-acetamide / 100 °C

2: CF₃COOH, pyrrole / CH₂Cl₂ / 0.17 h / Ambient temperature

3: pyridine / 0.5 h / 0 °C

4: AcOH / CH₂Cl₂ / 4 h / 0 °C

With pyridine; pyrrole; sodium hydride; acetic acid; trifluoroacetic acid; In dichloromethane; N,N-dimethyl acetamide;

DOI:10.1039/c39940000133

Reference yield:

5'-O-trityluridine (6554-10-5) → Benzoic acid (2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-bis-(2-nitro-phenyldisulfanyl)-tetrahydro-furan-2-ylmethyl ester (156592-87-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 4 h

2: 1.) NaH / N,N-dimethyl-acetamide / 100 °C

3: CF₃COOH, pyrrole / CH₂Cl₂ / 0.17 h / Ambient temperature

4: pyridine / 0.5 h / 0 °C

5: AcOH / CH₂Cl₂ / 4 h / 0 °C

With pyridine; pyrrole; sodium hydride; acetic acid; trifluoroacetic acid; In dichloromethane; N,N-dimethyl acetamide;

DOI:10.1039/c39940000133

upstream raw materials:

2-nitrobenzenesulfenyl chloride

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

benzoyl chloride

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione