(-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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Chemical Name:(-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
CAS No.:1392126-74-7
Molecular Formula:C₃₀H₃₀N₂O₆
Molecular Weight:514.578
Hs Code.:

Synonyms:(-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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Chemical Property of (-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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Technology Process of (-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

There total 7 articles about (-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-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: 74.0%

: 1392126-60-1
(-)-(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

: 1392126-74-7
(-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Guidance literature:: In dimethyl sulfoxide; at 90 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo3012754

Reference yield: 57.0%

: 1392126-57-6
(-)-(2R,3R,4R,5S)-1,3,4-tris(benzyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

: 1392126-74-7
(-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Guidance literature:: With aluminum isopropoxide; In dimethyl sulfoxide; at 180 ℃; for 0.166667h; Inert atmosphere; Microwave irradiation;
DOI:10.1021/jo3012754

Reference yield:

: 158226-97-2
(-)-(2R,3S,4R)-1,3,4-tris(benzyloxy)-5,5-bis(ethylthio)pentan-2-ol

: 1392126-74-7
(-)-1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 2.5 h / -40 - 0 °C / Inert atmosphere

2: 2,6-dimethylpyridine; N-Bromosuccinimide; water / acetone / 0.25 h / 0 °C / Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 16 h / 0 °C / Inert atmosphere

4: aluminum isopropoxide / dimethyl sulfoxide / 0.17 h / 180 °C / Inert atmosphere; Microwave irradiation

With 2,6-dimethylpyridine; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; water; aluminum isopropoxide; triethylamine; In dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1021/jo3012754