1,3-Dioxane-4-acetic acid, 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2-phenyl-, 1,1-dimethylethyl ester, (4R,6S)- synthesis

3synthesis methods

Product Name:1,3-Dioxane-4-acetic acid, 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2-phenyl-, 1,1-dimethylethyl ester, (4R,6S)-
CAS Number:1235588-97-2
Molecular formula:C33H40FN3O6S
Molecular Weight:625.75

124655-09-0 Synthesis

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester

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1,3-Dioxane-4-acetic acid, 6-[(1E)-2-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]ethenyl]-2-phenyl-, 1,1-dimethylethyl ester, (4R,6S)-

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Yield:-

Steps:

Multi-step reaction with 6 steps
1.1: 1H-imidazole; dmap / dichloromethane / 0.5 h / 20 °C
1.2: 3 h / 20 °C
2.1: acetic acid / tetrahydrofuran / 2 h / 20 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
5.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane / -15 - 20 °C
6.1: potassium carbonate / dimethyl sulfoxide / 1 h / 18 °C
6.2: 5 h / 60 °C

References:

KR2016/126700,2016,A

D-erythro-Hexonic acid, 2,4-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-3,5-O-(1-methylethylidene)-, 1,1-dimethylethyl ester

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References

154026-95-6 Synthesis

tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

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References