1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione
CAS No.:160509-66-0
Molecular Formula:C₂₄H₂₆N₂O₅
Molecular Weight:422.481
Hs Code.:

Synonyms:1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

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Chemical Property of 1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

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Technology Process of 1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

There total 19 articles about 1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-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:

: 149455-00-5
Acetic acid (1R,2R,3R,4R)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentylmethyl ester

: 160509-66-0
1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

Guidance literature:: With sodium methylate; In methanol;
DOI:10.1248/cpb.41.636

Reference yield:

: (3S,4R,5R)-3,4-Bis-benzyloxy-5-nitromethyl-tetrahydro-pyran-2-ol

: 160509-66-0
1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / CsF / dimethylformamide / 3 h / 25 °C

2: p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

3: 50 percent / CsF / dimethylformamide / 1 h / 25 °C

4: 30 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 1 h / 110 °C

5: 1percent sodium methoxide / methanol / 0.5 h / 25 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; cesium fluoride; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

: 149454-88-6
methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

: 160509-66-0
1-((1R,2R,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 12 steps

1: 80percent acetic acid / H₂O / 8 h / 50 °C

2: 1.) dibutyltin oxide; 2.) CsF / 1.) toluene, reflux, 3 h; 2.) DMF, 25 deg C, 2 h

3: 1.) (COCl)2, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -40 deg C, 6 h; 2.) CH₂Cl₂, 25 deg C, 30 min

4: KF, 18-crown-6 / dimethylformamide / 0.5 h / 25 °C

5: p-toluenesulfonic acid monohydrate / 25 °C

6: NaBH₄ / ethanol / 1 h / 25 °C

7: 57 percent / concd. HCl / acetic acid / 30 °C

8: 86 percent / CsF / dimethylformamide / 3 h / 25 °C

9: p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

10: 50 percent / CsF / dimethylformamide / 1 h / 25 °C

11: 30 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 1 h / 110 °C

12: 1percent sodium methoxide / methanol / 0.5 h / 25 °C

With hydrogenchloride; potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; cesium fluoride; In methanol; ethanol; water; acetic acid; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)89611-3