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

Base Information

• Chemical Name: (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ⁵-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one
• CAS No.: 329363-45-3
• Molecular Formula: C₄₃H₃₈NO₇P
• Molecular Weight: 711.751

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

Chemical Property of (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ⁵-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one

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Technology Process of (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ⁵-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one

There total 3 articles about (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ⁵-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one 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:

(R,R)-TADDOL (93379-48-7) → (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ5-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one (329363-45-3)

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:

(3aR,8aR)-6-chloro-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine (299917-90-1) → (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ5-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one (329363-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O; NEt₃ / tetrahydrofuran / 1 h / 0 °C

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

With N,N,N,N,-tetramethylethylenediamine; water; diethylzinc; triethylamine; In tetrahydrofuran;

DOI:10.1002/1521-3773(20001215)39:24<4605::AID-ANIE4605>3.0.CO;2-X

Reference yield:

1-[(E)-2-nitroethenyl]naphthalene (4735-49-3,37630-26-5) + (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) → (3aR,8aR)-2,2-dimethyl-6-[(1S)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ5-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one + (3aR,8aR)-2,2-dimethyl-6-[(1R)-1-(1-naphthyl)-2-nitroethyl]-4,4,8,8-tetraphenylperhydro-6λ5-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one (329363-45-3)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; diethylzinc; In tetrahydrofuran; at -78 ℃; for 12h;

DOI:10.1002/1521-3773(20001215)39:24<4605::AID-ANIE4605>3.0.CO;2-X

upstream raw materials:

1-[(E)-2-nitroethenyl]naphthalene

(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

(3aR,8aR)-6-chloro-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine

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