Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 182126-82-5
• Molecular Formula: C₂₅H₂₇N₃O₈S
• Molecular Weight: 529.571

Synonyms:Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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

Chemical Property:

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

There total 2 articles about Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl 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:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (182126-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrahydrofuran / 36 h / 60 °C / lipase from C_. antarctica

2: 2.) pyridine / 1.) THF, reflux, 2.) overnight

With pyridine; In tetrahydrofuran;

DOI:10.1021/jo9606259

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + benzylamine (100-46-9) + 5'-O-Carbophenoxythymidine (5864-33-5) → Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (182126-82-5)

Guidance literature:

With pyridine; Yield given. Multistep reaction; 1.) THF, reflux, 2.) overnight;

DOI:10.1021/jo9606259

Reference yield: 92.0%

Toluene-4-sulfonic acid (2R,3S,5R)-2-benzylcarbamoyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (182126-82-5) → 1-((4aS,6R,7aR)-1-Benzyl-2-oxo-hexahydro-furo[3,2-d][1,3]oxazin-6-yl)-5-methyl-1H-pyrimidine-2,4-dione (182126-65-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 2 h, 2.) room temperature, 5 h;

DOI:10.1021/jo9606259

upstream raw materials:

p-toluenesulfonyl chloride

benzylamine

5'-O-Carbophenoxythymidine

thymidine

Downstream raw materials:

1-((4aS,6R,7aR)-1-Benzyl-2-oxo-hexahydro-furo[3,2-d][1,3]oxazin-6-yl)-5-methyl-1H-pyrimidine-2,4-dione

1-((2R,4R,5S)-4-Benzylamino-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

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