(Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester

Base Information

• Chemical Name: (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester
• CAS No.: 342376-60-7
• Molecular Formula: C₃₃H₄₀N₂O₅S
• Molecular Weight: 576.757

Synonyms:(Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester

Chemical Property of (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester

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Technology Process of (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester

There total 3 articles about (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl 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: 70.0%

(Z)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-oxo-pent-2-enoic acid tert-butyl ester (342376-58-3) + methyl iodide (74-88-4) → (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester (342376-60-7) + (Z)-(S)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)00147-2

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester (342376-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1: KOtBu / tetrahydrofuran / 0.5 h / -78 °C

2: 80 percent / Me₃Al / toluene / 48 h / 50 °C

3: 70 percent / NaOH; TEBA-Cl / acetonitrile / 1 h / 20 °C

With sodium hydroxide; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; In tetrahydrofuran; toluene; acetonitrile; 1: Michael addition/1,3-prototropic shift;

DOI:10.1016/S0040-4039(01)00147-2

Reference yield:

2-(benzhydrylidene-amino)-pent-2-enedioic acid 1-tert-butyl ester 5-methyl ester (434331-68-7) → (Z)-(R)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-4-methyl-5-oxo-pent-2-enoic acid tert-butyl ester (342376-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Me₃Al / toluene / 48 h / 50 °C

2: 70 percent / NaOH; TEBA-Cl / acetonitrile / 1 h / 20 °C

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; trimethylaluminum; In toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)00147-2

upstream raw materials:

(Z)-2-(Benzhydrylidene-amino)-5-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-oxo-pent-2-enoic acid tert-butyl ester

methyl iodide

N-(diphenylmethylene)glycine tert-butyl ester

2-(benzhydrylidene-amino)-pent-2-enedioic acid 1-tert-butyl ester 5-methyl ester

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