Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

Base Information

Chemical Name:Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester
CAS No.:78080-93-0
Molecular Formula:C₂₂H₂₈N₂O₁₀S
Molecular Weight:512.538
Hs Code.:

Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

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Chemical Property of Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

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Technology Process of Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

There total 7 articles about Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl 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%

: 78080-92-9,78088-82-1
Acetic acid 4-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

: 78080-93-0,78080-94-1
Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

Guidance literature:: With formic acid; at 0 ℃;
DOI:10.1139/v81-127

Reference yield:

: 53658-45-0
2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl acetate

: 78080-93-0,78080-94-1
Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) pyridine, trifluoracetic acid, N,N'dicyclohexylcarbodiimide / 1.) dimethylsulfoxide, room temp., 18 h.; 2.) room temp., 24 h

2: 85 percent / NaBH₄ / ethanol / 0.08 h / -20 °C

3: 90 percent / H₂ / Pd/C / ethanol / 0.17 h / 760 Torr / Ambient temperature

4: 83 percent / pyridine / 0 °C

5: 75 percent / 90percent formic acid / 0 °C

With pyridine; sodium tetrahydroborate; formic acid; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol;
DOI:10.1139/v81-127

Reference yield:

: 362-43-6
2',3'-O-isopropylideneuridine

: 78080-93-0,78080-94-1
Acetic acid 4-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonyloxy)-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / CHCl₃ / 8 h / Heating

2: 1.) pyridine, trifluoracetic acid, N,N'dicyclohexylcarbodiimide / 1.) dimethylsulfoxide, room temp., 18 h.; 2.) room temp., 24 h

3: 85 percent / NaBH₄ / ethanol / 0.08 h / -20 °C

4: 90 percent / H₂ / Pd/C / ethanol / 0.17 h / 760 Torr / Ambient temperature

5: 83 percent / pyridine / 0 °C

6: 75 percent / 90percent formic acid / 0 °C

With pyridine; sodium tetrahydroborate; formic acid; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol; chloroform;
DOI:10.1139/v81-127