Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester

Base Information

• Chemical Name: Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester
• CAS No.: 199931-15-2
• Molecular Formula: C₃₄H₃₆N₂O₇
• Molecular Weight: 584.669
• Mol file: 199931-15-2.mol

Synonyms:Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester

Chemical Property of Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester

There total 13 articles about Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl 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: 53.0%

Benzoic acid 3-[(2R,3R,4R,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-pentafluorophenyloxythiocarbonyloxy-tetrahydro-furan-3-yl]-propyl ester (199931-16-3) → Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester (199931-15-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1080/07328319708006201

Reference yield:

1-[3-C-(3-benzoyloxypropyl)-3,5-di-O-benzyl-β-D-ribofuranosyl]thymine (199931-14-1) → Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester (199931-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / pyridine, DMAP / CH₂Cl₂ / Ambient temperature

2: 52 percent / AIBN, Bu₃SnH / benzene / 1 h / Heating

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; benzene;

Reference yield:

1-[3,5-Di-O-benzyl-3-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine (199931-19-6) → Benzoic acid 3-[(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-propyl ester (199931-15-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / Ambient temperature

2: 52 percent / pyridine, DMAP / CH₂Cl₂ / Ambient temperature

3: 52 percent / AIBN, Bu₃SnH / benzene / 1 h / Heating

With pyridine; 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; benzene;

upstream raw materials:

Benzoic acid 3-[(2R,3R,4R,5R)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-pentafluorophenyloxythiocarbonyloxy-tetrahydro-furan-3-yl]-propyl ester

benzoyl chloride

1-[3-C-(3-benzoyloxypropyl)-3,5-di-O-benzyl-β-D-ribofuranosyl]thymine

1-[3,5-Di-O-benzyl-3-C-(3-hydroxypropyl)-β-D-ribofuranosyl]thymine

Downstream raw materials:

3'-C-(3-benzoyloxypropyl)-5'-O-(4,4'-dimethoxytrityl)thymidine

3'-C-(3-benzoyloxypropyl)thymidine