N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

Base Information

Chemical Name:N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide
CAS No.:201946-58-9
Molecular Formula:C₂₅H₄₇NO₃Si₃
Molecular Weight:493.91
Hs Code.:

Synonyms:N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

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Chemical Property of N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

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Technology Process of N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

There total 5 articles about N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide 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:

: 201946-49-8
(R)-3-Hydroxy-2-(trimethylsilanylmethyl-amino)-propionic acid trimethylsilanylmethyl ester

: 201946-58-9
N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / imidazole / dimethylformamide / 18 h / 25 °C

2: 88 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

3: 95 percent / NaBH₄ / ethanol / 6 h / 25 °C

4: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, 25 deg C, 2.5 h

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo971706n

Reference yield:

: 201946-50-1
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(trimethylsilanylmethyl-amino)-propionic acid trimethylsilanylmethyl ester

: 201946-58-9
N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

2: 95 percent / NaBH₄ / ethanol / 6 h / 25 °C

3: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, 25 deg C, 2.5 h

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane;
DOI:10.1021/jo971706n

Reference yield:

: 201946-51-2
(R)-2-(Benzoyl-trimethylsilanylmethyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid trimethylsilanylmethyl ester

: 201946-58-9
N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / NaBH₄ / ethanol / 6 h / 25 °C

2: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, 25 deg C, 2.5 h

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1h, then 25 deg C, 3 h, 2.) THF, hexane, -78 deg C, 2 h, then 25 deg C, 0.5 h

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In ethanol;
DOI:10.1021/jo971706n