Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate

Base Information

• Chemical Name: Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate
• CAS No.: 1450880-23-5
• Molecular Formula: C₂₁H₂₅N₂O₈P
• Molecular Weight: 464.412
• Mol file: 1450880-23-5.mol

Synonyms:Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate

Chemical Property of Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate

There total 5 articles about Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate 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: 68.0%

Z-4-acetoxy-3-hydroxymethyl-buten-2-yl-phosphonate (1450880-21-3) + N-3-benzoylthymine (4330-20-5) → Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate (1450880-23-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 70 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol401922r

Reference yield:

2-hydroxypropane-1,3-diyl diacetate (105-70-4) → Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate (1450880-23-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 80 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

2.2: 3 h / -78 °C

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 h / 55 °C / Inert atmosphere; Sonication

4.1: Burkholderiacepacia lipase / aq. phosphate buffer / 48 h / 20 °C / pH 7 / Enzymatic reaction

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 h / 70 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; di-isopropyl azodicarboxylate; Burkholderiacepacia lipase; triphenylphosphine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; dimethyl sulfoxide; 5.1: |Mitsunobu Displacement;

DOI:10.1021/ol401922r

Reference yield:

1,3-diacetoxyacetone (6946-10-7) → Z-dimethyl-4’-(3-benzoyl-5-methyl-2,4-dioxo-pyrimidin-1-yl)-3’-(acetyloxymethyl)-but-2’-enylphosphonate (1450880-23-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C

1.2: 3 h / -78 °C

2.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 h / 55 °C / Inert atmosphere; Sonication

3.1: Burkholderiacepacia lipase / aq. phosphate buffer / 48 h / 20 °C / pH 7 / Enzymatic reaction

4.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 20 h / 70 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; di-isopropyl azodicarboxylate; Burkholderiacepacia lipase; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; 4.1: |Mitsunobu Displacement;

DOI:10.1021/ol401922r

upstream raw materials:

Z-4-acetoxy-3-hydroxymethyl-buten-2-yl-phosphonate

N-3-benzoylthymine

2-hydroxypropane-1,3-diyl diacetate

1,3-diacetoxyacetone