(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

Base Information

Chemical Name:(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil
CAS No.:725233-48-7
Molecular Formula:C₂₀H₂₃N₃O₈
Molecular Weight:433.418
Hs Code.:

Synonyms:(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

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Chemical Property of (-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

Chemical Property:

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Technology Process of (-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

There total 7 articles about (-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil 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: 47.0%

: 725233-46-5
(-)-1-{(1'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil

: [(3S,3aR,5R,6R,6aS)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-3-yl]-carbamic acid benzyl ester

: 725233-48-7
(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 24h;
DOI:10.1021/jo0496796

Reference yield:

: 725233-40-9
methyl 4-N-(tert-butoxycarbamoyl)-α-nitro-2-cyclopentenylacetate

: 725233-48-7
(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

Guidance literature:: Multi-step reaction with 6 steps

1: 972 mg / L-tartaric acid; NaBH₄; TiCl₃ / HCl; NaOH / H₂O; methanol / 4 h / pH 7.8

2: 95 percent / NaHCO₃ / tetrahydrofuran; H₂O

3: trifluoroacetic acid / CH₂Cl₂ / 0.75 h / cooling

4: tetrahydrofuran; benzene

5: 209 mg / sulfuric acid / methanol / 1 h / Heating

6: 43 percent / N-methylmorpholine N-oxide monohydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; titanium(III) chloride; L-Tartaric acid; sulfuric acid; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid; hydrogenchloride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1021/jo0496796

Reference yield:

: 189625-14-7
(2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester

: 725233-48-7
(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / NaOAc; Pd(OAc)2; PPh₃ / tetrahydrofuran / 20 °C

2: 972 mg / L-tartaric acid; NaBH₄; TiCl₃ / HCl; NaOH / H₂O; methanol / 4 h / pH 7.8

3: 95 percent / NaHCO₃ / tetrahydrofuran; H₂O

4: trifluoroacetic acid / CH₂Cl₂ / 0.75 h / cooling

5: tetrahydrofuran; benzene

6: 209 mg / sulfuric acid / methanol / 1 h / Heating

7: 43 percent / N-methylmorpholine N-oxide monohydrate; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

With palladium diacetate; sodium tetrahydroborate; osmium(VIII) oxide; titanium(III) chloride; L-Tartaric acid; sulfuric acid; sodium acetate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; hydrogenchloride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1021/jo0496796