(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 ethyl 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 ethyl ester
CAS No.:205513-91-3
Molecular Formula:C₂₄H₂₇N₃O₁₁
Molecular Weight:533.492
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 ethyl 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 ethyl 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 ethyl ester

There total 10 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 ethyl 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:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 205513-91-3
(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 ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) t-BuLi; 2.) O₃; 3.) M₂S / 1.) THF, -78 deg C; 2.) CH₂Cl₂; 3.) CH₂Cl₂

2: 83 percent / pyridine / CH₂Cl₂

3: 86 percent / CsF / dimethylformamide

4: 65 percent / EtONa / ethanol

5: 64 percent / pyridine / CH₂Cl₂

6: 86 percent / NaN₃ / dimethylformamide

7: Dowex 50 WH⁽¹⁺⁾ / Heating

8: pyridine

9: 88 percent / AcOH, conc. H₂SO₄ / CH₂Cl₂

10: 84 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Heating

11: hydrogen / 5percent Pd/BaSO₄ / methanol

12: 7percent aq. NaHCO₃ / dioxane

With pyridine; sodium azide; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; Dowex 50 WH⁽¹⁺⁾; sulfuric acid; hydrogen; tert.-butyl lithium; sodium ethanolate; sodium hydrogencarbonate; ozone; acetic acid; cesium fluoride; Pd-BaSO₄; In 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-97-S30

Reference yield:

: (S)-Azido-((2R,3S,4R,5R)-5-ethoxy-3,4-dihydroxy-tetrahydro-furan-2-yl)-acetic acid ethyl ester

: 205513-91-3
(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 ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine

2: 88 percent / AcOH, conc. H₂SO₄ / CH₂Cl₂

3: 84 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Heating

4: hydrogen / 5percent Pd/BaSO₄ / methanol

5: 7percent aq. NaHCO₃ / dioxane

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; hydrogen; sodium hydrogencarbonate; acetic acid; Pd-BaSO₄; In 1,4-dioxane; pyridine; methanol; dichloromethane;
DOI:10.3987/COM-97-S30

Reference yield:

: 211111-00-1
(S)-Azido-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid ethyl ester

: 205513-91-3
(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 ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Dowex 50 WH⁽¹⁺⁾ / Heating

2: pyridine

3: 88 percent / AcOH, conc. H₂SO₄ / CH₂Cl₂

4: 84 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Heating

5: hydrogen / 5percent Pd/BaSO₄ / methanol

6: 7percent aq. NaHCO₃ / dioxane

With trimethylsilyl trifluoromethanesulfonate; Dowex 50 WH⁽¹⁺⁾; sulfuric acid; hydrogen; sodium hydrogencarbonate; acetic acid; Pd-BaSO₄; In 1,4-dioxane; pyridine; methanol; dichloromethane;
DOI:10.3987/COM-97-S30