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

Base Information

Chemical Name:(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-hydroxy-ethyl)-amide
CAS No.:926627-22-7
Molecular Formula:C₂₆H₂₈NO₅P
Molecular Weight:465.486
Hs Code.:

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

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

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

There total 6 articles about (4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-hydroxy-ethyl)-amide 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:

: 917893-64-2
(2S,3R)-2,3-Dihydroxy-3-(2-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester

: 926627-22-7
(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-hydroxy-ethyl)-amide

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / p-toluenesulfonic acid / acetone / 16 h / 20 °C

2: 99 percent / N,N-diisopropylethylamine / palladium(II) acetate; 1,3-bis(diphenylphosphino)propane / dimethylsulfoxide / 3 h / 120 °C

3: 2 h / 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:

: 917893-65-3
(4S,5R)-2,2-Dimethyl-5-(2-trifluoromethanesulfonyloxy-phenyl)-[1,3]dioxolane-4-carboxylic acid ethyl ester

: 926627-22-7
(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-hydroxy-ethyl)-amide

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / N,N-diisopropylethylamine / palladium(II) acetate; 1,3-bis(diphenylphosphino)propane / dimethylsulfoxide / 3 h / 120 °C

2: 2 h / 120 °C

With N-ethyl-N,N-diisopropylamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; In dimethyl sulfoxide;
DOI:10.1016/j.tet.2006.05.043

Reference yield:

: 3943-94-0,17041-46-2,6236-62-0
(E)-ethyl 2-hydroxycinnamate

: 926627-22-7
(4S,5R)-5-[2-(Diphenyl-phosphinoyl)-phenyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (2-hydroxy-ethyl)-amide

Guidance literature:: Multi-step reaction with 5 steps

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

2: 79 percent / AD-mix-β; methanesulfonamide; H2O / 2-methyl-propan-2-ol / 48 h / 20 °C

3: 91 percent / p-toluenesulfonic acid / acetone / 16 h / 20 °C

4: 99 percent / N,N-diisopropylethylamine / palladium(II) acetate; 1,3-bis(diphenylphosphino)propane / dimethylsulfoxide / 3 h / 120 °C

5: 2 h / 120 °C

With 2,6-dimethylpyridine; methanesulfonamide; AD-mix-β; 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