(4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester
• CAS No.: 917893-80-2
• Molecular Formula: C₂₆H₂₇O₅P
• Molecular Weight: 450.471
• Mol file: 917893-80-2.mol

Synonyms:(4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Chemical Property of (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

There total 5 articles about (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl 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:

(4R,5S)-2,2-Dimethyl-5-(2-trifluoromethanesulfonyloxy-phenyl)-[1,3]dioxolane-4-carboxylic acid ethyl ester (917893-85-7) + Diphenylphosphine oxide (4559-70-0) → (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester (917893-80-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; In dimethyl sulfoxide; at 120 ℃;

DOI:10.1016/j.tet.2006.05.043

Reference yield:

(2R,3S)-2,3-Dihydroxy-3-(2-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester (917893-84-6) → (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester (917893-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / acetone

2: N,N-diisopropylethylamine / palladium(II) acetate; 1,3-bis(diphenylphosphino)propane / dimethylsulfoxide / 120 °C

With toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; In dimethyl sulfoxide; acetone;

DOI:10.1016/j.tet.2006.05.043

Reference yield:

(E)-ethyl 2-hydroxycinnamate (3943-94-0,17041-46-2,6236-62-0) → (4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester (917893-80-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 8.28 g / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 - 20 °C

2: AD-mix-α; methanesulfonamide; H2O / 2-methyl-propan-2-ol

3: p-toluenesulfonic acid / acetone

4: N,N-diisopropylethylamine / palladium(II) acetate; 1,3-bis(diphenylphosphino)propane / dimethylsulfoxide / 120 °C

With 2,6-dimethylpyridine; AD-mix-α; methanesulfonamide; water; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; In dichloromethane; dimethyl sulfoxide; acetone; tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tet.2006.05.043

upstream raw materials:

(4R,5S)-2,2-Dimethyl-5-(2-trifluoromethanesulfonyloxy-phenyl)-[1,3]dioxolane-4-carboxylic acid ethyl ester

Diphenylphosphine oxide

(2R,3S)-2,3-Dihydroxy-3-(2-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester

(E)-ethyl 2-hydroxycinnamate

Downstream raw materials:

(4R,5S)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ((S)-1-hydroxymethyl-2,2-dimethyl-propyl)-amide

(S)-4-tert-Butyl-2-{(4R,5S)-5-[2-(diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,5-dihydro-oxazole