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

Base Information

Chemical Name:(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide
CAS No.:870091-90-0
Molecular Formula:C₂₁H₃₇NO₄Si
Molecular Weight:395.615
Hs Code.:

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

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

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

There total 3 articles about (2R,3S)-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: 89.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 179945-11-0
(2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

: 870091-90-0
(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 1 ℃; for 0.25h;
DOI:10.1002/ejoc.200500206

Reference yield:

: 870091-89-7
(-)-(R)-4-benzyl-3-[(2R,3S)-5-(benzyloxy)-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one

: 870091-90-0
(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: AlMe₃ / hexane; tetrahydrofuran; CH₂Cl₂ / 0.12 h / -10 - 20 °C

1.2: 89 percent / CH₂Cl₂; hexane; tetrahydrofuran / 4.25 h / 0 - 20 °C

2.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 1 °C

With 2,6-dimethylpyridine; trimethylaluminum; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.200500206

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 870091-90-0
(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,2-dimethylpentanamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: dibutylboron triflate; Et₃N / CH₂Cl₂ / 0.67 h / Cooling

1.2: CH₂Cl₂ / 3.5 h / -77 - 0 °C

1.3: 80 percent / aq. H₂O₂; phosphate buffer / CH₂Cl₂ / 0.5 h / 0 °C / pH 7.0

2.1: AlMe₃ / hexane; tetrahydrofuran; CH₂Cl₂ / 0.12 h / -10 - 20 °C

2.2: 89 percent / CH₂Cl₂; hexane; tetrahydrofuran / 4.25 h / 0 - 20 °C

3.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 1 °C

With 2,6-dimethylpyridine; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Evans syn-selective aldol reaction;
DOI:10.1002/ejoc.200500206