(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Base Information

Chemical Name:(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester
CAS No.:215440-27-0
Molecular Formula:C₂₃H₂₅N₃O₁₁
Molecular Weight:519.465
Hs Code.:

(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

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Chemical Property of (S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

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Technology Process of (S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

There total 13 articles about (S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester 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:

: 58934-96-6
1-(Methyl 2',3'-di-O-acetyl-5'-azido-5'-deoxy-β-D-allofuranosyluronate)uracil

: 215440-27-0
(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / methanol / Ambient temperature

2: NaHCO₃, H₂O / dioxane / 1 h / Ambient temperature

With water; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In 1,4-dioxane; methanol;
DOI:10.1055/s-1998-4499

Reference yield:

: 824411-64-5
1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-2-en-1-one

: 215440-27-0
(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / Zn(BH₄)2; CeCl₃*7H₂O / methanol; diethyl ether / 1 h / -10 °C

2: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

3: 69 percent / [bis(tricyclohexylphosphine)benzylideneruthenium(IV)]Cl₂ / CH₂Cl₂ / 24 h / Heating

4: 77 percent / aq. citric acid; K₂OsO₂(OH)4; NMO / acetone / 16 h / 20 °C

5: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

6: 0.681 g / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

7: 80 percent / aq. formic acid / CH₂Cl₂ / 20 h / 0 °C

8: RuCl₃*3H₂O; NaIO₄ / acetonitrile; CCl₄; H₂O / 0.5 h / 20 °C

9: 0.291 g / diethyl ether / 0.5 h

10: 76 percent / TMSOTf / 1,2-dichloro-ethane / 5 h / 20 °C

With pyridine; Grubbs catalyst first generation; dmap; ruthenium trichloride; sodium periodate; formic acid; N-methyl-2-indolinone; cerium(III) chloride; zinc(II) tetrahydroborate; potassium dioxotetrahydroxoosmate(VI); trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; citric acid; In methanol; tetrachloromethane; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile;
DOI:10.1021/jo048586l

Reference yield:

: 1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-2-en-1-ol

: 215440-27-0
(S)-Benzyloxycarbonylamino-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

2: 69 percent / [bis(tricyclohexylphosphine)benzylideneruthenium(IV)]Cl₂ / CH₂Cl₂ / 24 h / Heating

3: 77 percent / aq. citric acid; K₂OsO₂(OH)4; NMO / acetone / 16 h / 20 °C

4: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

5: 0.681 g / pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

6: 80 percent / aq. formic acid / CH₂Cl₂ / 20 h / 0 °C

7: RuCl₃*3H₂O; NaIO₄ / acetonitrile; CCl₄; H₂O / 0.5 h / 20 °C

8: 0.291 g / diethyl ether / 0.5 h

9: 76 percent / TMSOTf / 1,2-dichloro-ethane / 5 h / 20 °C

With pyridine; Grubbs catalyst first generation; dmap; ruthenium trichloride; sodium periodate; formic acid; N-methyl-2-indolinone; potassium dioxotetrahydroxoosmate(VI); trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; citric acid; In tetrachloromethane; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile;
DOI:10.1021/jo048586l