1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione
CAS No.:129678-54-2
Molecular Formula:C₂₆H₃₂N₂O₆Si
Molecular Weight:496.635
Hs Code.:

Synonyms:1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

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Chemical Property of 1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

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MSDS Files:: SDS file from LookChem

Useful:

Technology Process of 1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

There total 4 articles about 1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]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: 70.0%

: 129678-52-0
(2S,3S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-carbaldehyde

: 129678-54-2
1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Guidance literature:: With sodium tetrahydroborate; In ethanol; water; for 0.5h; Ambient temperature;
DOI:10.1021/jm00171a025

Reference yield:

: 130351-52-9
1-<3-deoxy-3-C-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-β-D-arabino-pentofuranosyl>uracil

: 129678-54-2
1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

3: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00171a025

Reference yield:

: 96253-10-0
1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione

: 129678-54-2
1-[(2R,3S,4S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min

2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature

3: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature

4: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H₂O / 0.08 h / 0 °C

5: 70 percent / sodium borohydride / ethanol; H₂O / 0.5 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; triethylamine; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1021/jm00171a025