dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate

Base Information

• Chemical Name: dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate
• CAS No.: 186704-15-4
• Molecular Formula: C₂₀H₂₅O₅P
• Molecular Weight: 376.389
• Mol file: 186704-15-4.mol

Synonyms:dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate

Chemical Property of dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate

There total 8 articles about dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-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: 40.0%

Dibenzyl phosphite (17176-77-1) + (R)-(2-isopropenyloxiran-2-yl)methanol (186704-14-3) → dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate (186704-15-4)

Guidance literature:

With isopropylmagnesium chloride; In diethyl ether; at -50 - 0 ℃; for 2.5h;

DOI:10.1016/S0040-4039(96)02319-2

Reference yield:

3-methyl-2-methylenebut-3-en-1-ol (26431-13-0) → dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate (186704-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: D-DET, Ti(i-PrO)4, TBHP / CH₂Cl₂ / 24 h / -20 °C

2: 40 percent / isopropyl magnesium chloride / diethyl ether / 2.5 h / -50 - 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; isopropylmagnesium chloride; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(96)02319-2

Reference yield:

1-chloro-2-(chloromethyl)-3-methylbut-3-en-2-ol (729592-76-1) → dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate (186704-15-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 73 percent / NaOH / 66 h / 50 °C

2.1: porcine pancreatic lipase / 5 h / 20 °C

3.1: 71 percent / p-toluenesulfonyl chloride; 4-(N,N-dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 72 h / 20 °C

4.1: 90 percent / Candida antarctica lipase; ethanol / diethyl ether / 72 h / 20 °C

5.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -78 °C

5.2: 40 percent / tetrahydrofuran / -78 - 0 °C

With dmap; Candida antarctica lipase; sodium hydroxide; porcine pancreatic lipase; ethanol; isopropylmagnesium chloride; triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tetasy.2004.04.046

upstream raw materials:

Dibenzyl phosphite

(R)-(2-isopropenyloxiran-2-yl)methanol

1-chloro-2-(chloromethyl)-3-methylbut-3-en-2-ol

2-isopropenylpropane-1,2,3-triol

Downstream raw materials:

((S)-2-Hydroxy-2-hydroxymethyl-3-oxo-butyl)-phosphonic acid dibenzyl ester