1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:199458-13-4
Molecular Formula:C₂₉H₃₅N₅O₈
Molecular Weight:581.626
Hs Code.:

1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

There total 10 articles about 1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione 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:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 199458-13-4
1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / NaH, nBu₄NI / tetrahydrofuran / 12 h / Ambient temperature

2: 89 percent / 90percent AcOH / H₂O / 2.5 h / 40 °C

3: 82 percent / Et₃N, pyridine, DMAP / CH₂Cl₂ / 2.5 h / 0 - 25 °C

4: 80 percent / NaI, nBu₃SnH, AIBN / 1,2-dimethoxy-ethane / 1.5 h / 80 °C

5: 80 percent / Et₃N, DMAP / pyridine / 3.5 h / 70 °C

6: 88 percent / NaN₃ / dimethylformamide / 1.5 h / 80 °C

7: 47 percent / CF₃COOH / CH₂Cl₂; H₂O / 16 h / Ambient temperature

8: 97 percent / pyridine

With pyridine; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-1003

Reference yield:

: 69940-04-1,142226-16-2,109536-51-8
(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

: 199458-13-4
1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / Et₃N, pyridine, DMAP / CH₂Cl₂ / 2.5 h / 0 - 25 °C

2: 80 percent / NaI, nBu₃SnH, AIBN / 1,2-dimethoxy-ethane / 1.5 h / 80 °C

3: 80 percent / Et₃N, DMAP / pyridine / 3.5 h / 70 °C

4: 88 percent / NaN₃ / dimethylformamide / 1.5 h / 80 °C

5: 47 percent / CF₃COOH / CH₂Cl₂; H₂O / 16 h / Ambient temperature

6: 97 percent / pyridine

With pyridine; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; trifluoroacetic acid; sodium iodide; In pyridine; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-1003

Reference yield:

: 69940-02-9,142226-15-1,115693-78-2
3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 199458-13-4
1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / 90percent AcOH / H₂O / 2.5 h / 40 °C

2: 82 percent / Et₃N, pyridine, DMAP / CH₂Cl₂ / 2.5 h / 0 - 25 °C

3: 80 percent / NaI, nBu₃SnH, AIBN / 1,2-dimethoxy-ethane / 1.5 h / 80 °C

4: 80 percent / Et₃N, DMAP / pyridine / 3.5 h / 70 °C

5: 88 percent / NaN₃ / dimethylformamide / 1.5 h / 80 °C

6: 47 percent / CF₃COOH / CH₂Cl₂; H₂O / 16 h / Ambient temperature

7: 97 percent / pyridine

With pyridine; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide; In pyridine; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-1003