Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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Chemical Name:Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
CAS No.:90661-45-3
Molecular Formula:C₂₂H₂₅N₅O₈
Molecular Weight:487.469
Hs Code.:

Synonyms:Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 11 articles about Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl 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: 98.0%

: 90661-44-2
Acetic acid (2R,3R,4R)-4,5-diacetoxy-2-((R)-1-azido-2-benzyloxy-ethyl)-tetrahydro-furan-3-yl ester

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 90661-45-3
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In chloroform; Heating;
DOI:10.1246/cl.1984.405

Reference yield:

: 90661-42-0
(S)-5-[(S)-2-Benzyloxy-1-(methyl-diphenyl-silanyloxy)-ethyl]-5H-furan-2-one

: 90661-45-3
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: KMnO₄ / dicyclohexano-18-crown-6 / CH₂Cl₂ / -42 °C

2: p-TsOH / CH₂Cl₂ / Ambient temperature

3: 75 percent / KF / n-Bu₄N(+)*HSO₄(-) / H₂O; CH₂Cl₂

4: Et₃N / Ambient temperature

5: 71 percent / LiN₃ / hexamethylphosphoric acid triamide / 80 °C

6: DIBAH / toluene / -78 °C

7: 70percent AcOH / 80 °C

8: 97 percent / pyridine / 0 °C

9: 98 percent / TMSOTf / CHCl₃ / Heating

With potassium fluoride; potassium permanganate; lithium azide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; perhydrodibenzo-18-crown-6; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform; water; toluene;
DOI:10.1246/cl.1984.405

Reference yield:

: 90661-40-8
(S)-5-((S)-2'-(benzyloxy)-1-hydroxyethyl)furan-2(5H)-one

: 90661-45-3
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: KMnO₄ / dicyclohexano-18-crown-6 / CH₂Cl₂ / -42 °C

3: p-TsOH / CH₂Cl₂ / Ambient temperature

4: 75 percent / KF / n-Bu₄N(+)*HSO₄(-) / H₂O; CH₂Cl₂

5: Et₃N / Ambient temperature

6: 71 percent / LiN₃ / hexamethylphosphoric acid triamide / 80 °C

7: DIBAH / toluene / -78 °C

8: 70percent AcOH / 80 °C

9: 97 percent / pyridine / 0 °C

10: 98 percent / TMSOTf / CHCl₃ / Heating

With 2,6-dimethylpyridine; potassium fluoride; potassium permanganate; lithium azide; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; perhydrodibenzo-18-crown-6; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform; water; toluene;
DOI:10.1246/cl.1984.405