isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate

Base Information

• Chemical Name: isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• CAS No.: 808162-99-4
• Molecular Formula: C₂₈H₃₈FN₃O₆S
• Molecular Weight: 563.691
• Mol file: 808162-99-4.mol

Synonyms:isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate

Chemical Property of isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate

There total 10 articles about isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate 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: 68.3%

N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (289042-10-0) + isopropyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (808163-02-2) → isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate (808162-99-4)

Guidance literature:

N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -65 ℃; for 0.5h;

isopropyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; In tetrahydrofuran; toluene; at -65 - 10 ℃; for 2.16667h;

Reference yield:

[4-[4-fluorophenyl-6-(1-methylethyl)-2-[N-methyl-(N-methanesulfonyl)amino]]-5-pyrimidinyl]methylphenyltriphenylphosphonium bromide + isopropyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (808163-02-2) → isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate (808162-99-4)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 70 ℃; for 3.5h; Time; Inert atmosphere;

DOI:10.1055/s-0035-1562787

Reference yield:

C25H25O5(1-)*Na(1+) → isopropyl 2-[(4R,6S)-6-{(E)-2-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]vinyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate (808162-99-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,N-dimethyl-formamide / 37 h / 65 °C

2.1: iron(III) chloride hexahydrate / dichloromethane / 3 h / -10 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 0.17 h / -10 °C / Inert atmosphere

3.2: 4 h / -78 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / acetone / 15 h / 20 °C / Inert atmosphere

5.1: sodium methylate / methanol / 2 h / -10 °C / Inert atmosphere

6.1: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / -5 °C / pH 9 - 9.5

7.1: potassium carbonate / dimethyl sulfoxide / 3.5 h / 70 °C / Inert atmosphere

With pyridine; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iron(III) chloride hexahydrate; sodium methylate; pyridinium p-toluenesulfonate; potassium carbonate; potassium bromide; In methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 7.1: |Wittig Olefination;

DOI:10.1055/s-0035-1562787

upstream raw materials:

N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide

isopropyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

5-O-(triphenylmethyl)-3-deoxy-1,2-anhydro-D-erythro-pentitol

(3S,5S)-3,5-dihydroxy-6-(trityloxy)hexanenitrile

Downstream raw materials:

(3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine