2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester
CAS No.:136399-55-8
Molecular Formula:C₂₅H₃₂N₂O₉
Molecular Weight:504.537
Hs Code.:

2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

Synonyms:2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

There total 8 articles about 2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-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: 85.0%

: N,O-Bis(TMS)uracil

: 2,2-Dimethyl-propionic acid (3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-4-methoxy-2-phenylsulfanyl-tetrahydro-furan-3-yl ester

: 136399-55-8
2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -20 - 0 ℃;
DOI:10.1021/jo00081a004

Reference yield: 3.0%

: 136399-54-7
2,2-Dimethyl-propionic acid (2S,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-4-methoxy-2-phenylsulfanyl-tetrahydro-furan-3-yl ester

: 10457-14-4
O,O'-bis-(trimethylsilyl)uracil

: 136399-55-8
2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

: 136399-56-9
2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(5-iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at -10 ℃; for 0.166667h;
DOI:10.1016/S0040-4039(00)79751-6

Reference yield:

: 18968-50-8,29587-02-8,32166-85-1,36215-54-0,43138-65-4,65725-74-8,67816-77-7
1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

: 136399-55-8
2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

2: Et₃N, DMAP / CH₂Cl₂

3: 80percent AcOH / 2 h / 90 °C

4: Et₃N / benzene

5: 80 percent / TMSOTf / CCl₄ / 6 h / Heating

6: 85 percent / NIS, TfOH / CH₂Cl₂ / -20 - 0 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; acetic acid; triethylamine; In tetrachloromethane; dichloromethane; benzene;
DOI:10.1021/jo00081a004