(2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Base Information

Chemical Name:(2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide
CAS No.:787552-69-6
Molecular Formula:C₂₁H₃₇NO₄Si
Molecular Weight:395.615
Hs Code.:

Synonyms:(2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

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Technology Process of (2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

There total 3 articles about (2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide 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: 68.0%

: 787552-68-5
(2S,3R)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

: 18162-48-6
tert-butyldimethylsilyl chloride

: 787552-69-6
(2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 43h;
DOI:10.1016/j.tet.2004.07.059

Reference yield:

: 787552-67-4
(S)-4-benzyl-3-((2S,3R)-5-benzyloxy-3-hydroxy-2-methylpentanoyl)-2-oxazolidinone

: 787552-69-6
(2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: AlMe₃ / tetrahydrofuran / -10 - 20 °C

1.2: 82 percent / CH₂Cl₂; tetrahydrofuran / -10 - 0 °C

2.1: 68 percent / imidazole / dimethylformamide / 43 h / 20 °C

With 1H-imidazole; trimethylaluminum; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.07.059

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 787552-69-6
(2S,3R)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0.67 h / 0 - 2 °C

1.2: CH₂Cl₂ / -77 - 0 °C

1.3: 71 percent / H₂O₂ / aq. phosphate buffer; methanol; CH₂Cl₂ / 0.5 h / 0 °C

2.1: AlMe₃ / tetrahydrofuran / -10 - 20 °C

2.2: 82 percent / CH₂Cl₂; tetrahydrofuran / -10 - 0 °C

3.1: 68 percent / imidazole / dimethylformamide / 43 h / 20 °C

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.07.059