N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide
• CAS No.: 459457-08-0
• Molecular Formula: C₂₉H₃₆INO₄SSi
• Molecular Weight: 649.665

Synonyms:N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

Chemical Property of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

There total 10 articles about N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 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: 100.0%

N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-07-9) → N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-08-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1016/S0040-4039(02)00833-X

Reference yield:

(2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid (34235-88-6) → N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-08-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: KHCO₃ / dimethylformamide

2.1: LiBH₄ / tetrahydrofuran

3.1: TsOH / CH₂Cl₂

4.1: 96 percent / NaH / dimethylformamide

5.1: OsO₄; NMO / acetone; H₂O

5.2: NaIO₄ / tetrahydrofuran; various solvent(s)

5.3: 100 percent / NaBH₄ / methanol

6.1: 97 percent / I₂; Ph₃P; imidazole / toluene

7.1: aq. HCl; tetrahydrofuran

8.1: imidazole / dimethylformamide

9.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂

With 1H-imidazole; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; iodine; sodium hydride; potassium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(02)00833-X

Reference yield:

(2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate (43188-53-0) → N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-08-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LiBH₄ / tetrahydrofuran

2.1: TsOH / CH₂Cl₂

3.1: 96 percent / NaH / dimethylformamide

4.1: OsO₄; NMO / acetone; H₂O

4.2: NaIO₄ / tetrahydrofuran; various solvent(s)

4.3: 100 percent / NaBH₄ / methanol

5.1: 97 percent / I₂; Ph₃P; imidazole / toluene

6.1: aq. HCl; tetrahydrofuran

7.1: imidazole / dimethylformamide

8.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂

With 1H-imidazole; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; iodine; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(02)00833-X

upstream raw materials:

N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

(2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid

(2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate

p-toluenesulfonyl chloride

Downstream raw materials:

(2R,3R)-2-hydroxymethyl-3-methyl-1-(toluene-4-sulfonyl)pyrrolidin-3-ol

(2S,3R)-3-hydroxy-3-methylpyrrolidine-2-carboxylic acid

N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

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