Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 177779-38-3
• Molecular Formula: C₂₅H₂₆N₂O₈S
• Molecular Weight: 514.556

Synonyms:

Chemical Property of Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

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Technology Process of Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

There total 6 articles about Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-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: 54.0%

5-thien-2-yl-1-(β-D-2-deoxyribofuranos-1-yl)uracil (89647-10-9) + glutaric acid chloride monobenzyl ester (67852-85-1) → Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (177779-38-3)

Guidance literature:

In pyridine; dichloromethane; for 2.5h;

DOI:10.1080/07328319608002034

Reference yield:

glutaric acid monobenzyl ester (54322-10-0) → Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (177779-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / 120 h / 0 deg C to rt

2: 54 percent / pyridine; CH₂Cl₂ / 2.5 h

With oxalyl dichloride; In pyridine; dichloromethane;

DOI:10.1080/07328319608002034

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → Pentanedioic acid benzyl ester (2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-yl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (177779-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / CuI / CHCl₃

2: 95 percent / NaOMe / methanol / 24 h / Ambient temperature

3: 54 percent / pyridine; CH₂Cl₂ / 2.5 h

With copper(l) iodide; sodium methylate; In pyridine; methanol; dichloromethane; chloroform;

DOI:10.1080/07328319608002034

upstream raw materials:

5-thien-2-yl-1-(β-D-2-deoxyribofuranos-1-yl)uracil

glutaric acid chloride monobenzyl ester

glutaric acid monobenzyl ester

β-5-(2''-thienyl)-2'-deoxy-3',5'-di-O-toluoyluridine

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