(4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

Base Information

Chemical Name:(4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]
CAS No.:247061-34-3
Molecular Formula:C₄₆H₅₈I₂N₂O₄Si₂
Molecular Weight:1012.96
Hs Code.:

Synonyms:(4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

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Chemical Property of (4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

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Technology Process of (4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

There total 6 articles about (4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 247061-33-2
(4S,5S)-4,5-Dihydroxy-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

: 247061-34-3
(4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

Guidance literature:: With 1H-imidazole; In dichloromethane;
DOI:10.1021/ja991714g

Reference yield:

: 615-43-0
2-iodophenylamine

: 247061-34-3
(4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / Me₃Al / toluene / 20 °C

2: 87 percent / NaH / dimethylformamide

3: 70 percent / BCl₃ / -78 °C

4: 86 percent / imidazole / CH₂Cl₂

With 1H-imidazole; trimethylaluminum; boron trichloride; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: N-benzylation / 3: debenzylation / 4: silylation;
DOI:10.1021/ja991714g

Reference yield:

: 247061-46-7
(4S,5S)-4,5-Bis-benzyloxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

: 247061-34-3
(4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-ene-1,2-dicarboxylic acid bis-[benzyl-(2-iodo-phenyl)-amide]

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: 72 percent / I₂ / tetrahydrofuran / -78 °C

2.1: 92 percent / Me₃Al / toluene / 20 °C

3.1: 87 percent / NaH / dimethylformamide

4.1: 70 percent / BCl₃ / -78 °C

5.1: 86 percent / imidazole / CH₂Cl₂

With 1H-imidazole; trimethylaluminum; boron trichloride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Oxidation / 2.1: Condensation / 3.1: N-benzylation / 4.1: debenzylation / 5.1: silylation;
DOI:10.1021/ja991714g