Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propyl ester

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Chemical Name:Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propyl ester
CAS No.:78106-10-2
Molecular Formula:C₂₃H₃₀N₂O₉S
Molecular Weight:510.565
Hs Code.:

Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propyl ester

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

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

There total 9 articles about Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-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: 89.0%

: 78081-01-3,78081-02-4
Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(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]-propyl ester

: 78106-10-2,78106-11-3
Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propyl ester

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

Reference yield:

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

: 78106-10-2,78106-11-3
Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propyl ester

Guidance literature:: Multi-step reaction with 9 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: 97 percent / NaOMe / CHCl₃ / 0 °C

7: 88 percent / various solvent(s) / 8 h / 45 - 50 °C

8: 94 percent / pyridine / 0 °C

9: 89 percent / 90percent formic acid / 0 °C

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

Reference yield:

: 78080-87-2
1-<(E)-8-O-acetyl-5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-oct-5-eno-1,4-furanosid-7-ulosyl>-3-methyluracil

: 78106-10-2,78106-11-3
Toluene-4-sulfonic acid 1-allyloxymethyl-3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / NaBH₄ / ethanol / 0.08 h / -20 °C

2: 90 percent / H₂ / Pd/C / ethanol / 0.17 h / 760 Torr / Ambient temperature

3: 83 percent / pyridine / 0 °C

4: 97 percent / NaOMe / CHCl₃ / 0 °C

5: 88 percent / various solvent(s) / 8 h / 45 - 50 °C

6: 94 percent / pyridine / 0 °C

7: 89 percent / 90percent formic acid / 0 °C

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