1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione
CAS No.:1054632-55-1
Molecular Formula:C₁₈H₁₉N₃O₇
Molecular Weight:389.365
Hs Code.:

Synonyms:1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

There total 13 articles about 1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-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:

: 874812-56-3
(1R,3R,4S,5R)-3-benzyloxymethyl-4-benzyloxy-6-N-(phenoxyacetyl)-1-(uracil-1-yl)-6-aza-2-oxabicyclo[3.2.0]heptane

: 1054632-55-1
1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: With boron trichloride; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo052115x

Reference yield:

: 1-((2R,3R,4S,5R)-5-Benzyloxymethyl-3,4-dihydroxy-2-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

: 1054632-55-1
1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 12 steps

1: 3.1 g / pyridine / 24 h / 20 °C

2: 91 percent / diphenyl carbonate; NaHCO₃ / dimethylformamide / 2 h / 110 °C

3: 85 percent / NaH / acetonitrile / 0 - 20 °C

4: 79 percent / aq. AcOH / 48 h / 20 °C

5: 89 percent / pyridine / 1.5 h / 0 °C

6: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

7: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

8: 90 percent / pyridine / 24 h / 0 °C

9: 90 percent / PMe₃; H₂O / tetrahydrofuran / 1 h / 20 °C

10: 63 percent / pyridine; Et₃N / 48 h / 90 °C

11: 84 percent / pyridine / 2.5 h / 20 °C

12: BCl₃ / CH₂Cl₂ / -78 - 20 °C

With pyridine; bis(phenyl) carbonate; sodium hydroxide; sodium azide; water; boron trichloride; sodium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo052115x

Reference yield:

: 874812-49-4
(2R,3R,3aS,9aR)-3-Benzyloxy-2-benzyloxymethyl-9a-hydroxymethyl-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one

: 1054632-55-1
1-[(1R,3R,4S,5R)-4-Hydroxy-3-hydroxymethyl-6-(2-phenoxy-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-1-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / pyridine / 1.5 h / 0 °C

2: 87 percent / NaN₃ / dimethylformamide / 60 h / 100 °C

3: 85 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C

4: 90 percent / pyridine / 24 h / 0 °C

5: 90 percent / PMe₃; H₂O / tetrahydrofuran / 1 h / 20 °C

6: 63 percent / pyridine; Et₃N / 48 h / 90 °C

7: 84 percent / pyridine / 2.5 h / 20 °C

8: BCl₃ / CH₂Cl₂ / -78 - 20 °C

With pyridine; sodium hydroxide; sodium azide; water; boron trichloride; triethylamine; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo052115x