2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester

Base Information

• Chemical Name: 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester
• CAS No.: 380356-19-4
• Molecular Formula: C₄₃H₄₁O₉P
• Molecular Weight: 732.767

Synonyms:

Chemical Property of 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester

Chemical Property:

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Technology Process of 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester

There total 2 articles about 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl 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: 64.0%

dimethyl 2-benzylidenepropanedioate (6626-84-2) + (3aR,8aR)-2,2-dimethyl-4,4,8,8-tetraphenylperhydro-6λ5-[1,3]dioxolo-[4,5-e][1,3,2]dioxaphosphepin-6-one (329363-38-4) → 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ5-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester (380356-19-4) + 2-{(R)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ5-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester

Guidance literature:

With iron(III) oxide; potassium hydroxide; water; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol016591v

Reference yield:

(R,R)-TADDOL (93379-48-7) → 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ5-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester (380356-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: PCl₃; Et₃N / tetrahydrofuran / 2 h / 0 °C

1.2: 95 percent / aq. H₂O / tetrahydrofuran / 1 h

2.1: Et₂Zn; TMEDA / tetrahydrofuran; heptane / 12 h / -78 °C

With N,N,N,N,-tetramethylethylenediamine; diethylzinc; triethylamine; phosphorus trichloride; In tetrahydrofuran; n-heptane; 2.1: asymmetric Michael addition;

DOI:10.1055/s-2006-926437

Reference yield:

2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ5-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester (380356-19-4) → 2-((S)-Phenyl-phosphono-methyl)-malonic acid

Guidance literature:

2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-phenylmethyl}malonic acid dimethyl ester; With chloro-trimethyl-silane; sodium iodide; In acetonitrile; Heating;

With water; In dichloromethane; Further stages.;

DOI:10.1021/ol016591v

upstream raw materials:

dimethyl 2-benzylidenepropanedioate

(3aR,8aR)-2,2-dimethyl-4,4,8,8-tetraphenylperhydro-6λ⁵-[1,3]dioxolo-[4,5-e][1,3,2]dioxaphosphepin-6-one

(R,R)-TADDOL

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