Pentanedioic acid (2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-allyloxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Pentanedioic acid (2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-allyloxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 876403-54-2
• Molecular Formula: C₃₈H₄₄N₄O₁₃
• Molecular Weight: 764.786

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

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

Chemical Property:

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

There total 6 articles about Pentanedioic acid (2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-allyloxy-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: 88.0%

Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester (876403-52-0) + 3’-allyl ether thymidine (211191-57-0) → Pentanedioic acid (2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-allyloxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (876403-54-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; toluene; at 20 ℃; for 24h;

DOI:10.1081/NCN-60595

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → Pentanedioic acid (2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-allyloxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (876403-54-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine; 4-dimethylaminopyridine / 20 °C

2: 79 percent / NaH / tetrahydrofuran / 4 h / ultrasonication

3: 88 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4: 88 percent / 4-(dimethylamino)pyridine; DCC / CH₂Cl₂; toluene / 24 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1081/NCN-60595

Reference yield:

3-N-benzoyl-5'-O-(prop-2-enyl)thymidine (876403-50-8) → Pentanedioic acid (2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-allyloxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (876403-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / 4-(dimethylamino)pyridine; pyridine / 5 h / 60 °C

2: 88 percent / 4-(dimethylamino)pyridine; DCC / CH₂Cl₂; toluene / 24 h / 20 °C

With pyridine; dmap; dicyclohexyl-carbodiimide; In dichloromethane; toluene;

DOI:10.1081/NCN-60595

upstream raw materials:

Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

3’-allyl ether thymidine

3-N-benzoyl-5'-O-(prop-2-enyl)thymidine

5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

Downstream raw materials:

3-Benzoyl-5-methyl-1-[(Z)-(1S,9R,11R,13S,22R,24R)-24-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-15,19-dioxo-2,7,10,14,20,23-hexaoxa-tricyclo[20.3.0.0^9,13]pentacos-4-en-11-yl]-1H-pyrimidine-2,4-dione

3-Benzoyl-5-methyl-1-[(E)-(1S,9R,11R,13S,22R,24R)-24-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-15,19-dioxo-2,7,10,14,20,23-hexaoxa-tricyclo[20.3.0.0^9,13]pentacos-4-en-11-yl]-1H-pyrimidine-2,4-dione

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