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

Base Information

• Chemical Name: Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 167641-88-5
• Molecular Formula: C₁₇H₁₇IN₂O₅
• Molecular Weight: 456.237
• Mol file: 167641-88-5.mol

Synonyms:Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-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: 75.0%

2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine (70838-44-7) → Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (167641-88-5)

Guidance literature:

With magnesium iodide; In toluene; at 110 ℃;

DOI:10.1016/0040-4039(94)02383-M

Reference yield:

Benzoic acid (2R,3S)-5-(diethoxy-phosphanyloxy)-3-iodo-tetrahydro-furan-2-ylmethyl ester (243971-82-6) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (167641-88-5) + Benzoic acid (2R,3S,5S)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In various solvent(s); at -50 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1055/s-1999-3166

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2R,3S,5R)-3-iodo-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (167641-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂

2: BCl₃*SMe₂ / diethyl ether / 0.5 h

3: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

4: TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; boron trichloride - methyl sulfide complex; triethylamine; In diethyl ether; dichloromethane; 1: Acylation / 2: Deallylation / 3: Substitution / 4: Substitution;

DOI:10.1055/s-1999-3166

upstream raw materials:

2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine

Benzoic acid (2R,3S)-5-(diethoxy-phosphanyloxy)-3-iodo-tetrahydro-furan-2-ylmethyl ester

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

benzoyl chloride

Downstream raw materials:

1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)thymine

3'-α-C-allenyl-5'-O-benzoyl-2',3'-dideoxythymidine