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

Base Information

• Chemical Name: (2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide
• CAS No.: 179945-11-0
• Molecular Formula: C₁₅H₂₃NO₄
• Molecular Weight: 281.352
• Mol file: 179945-11-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2R,3S)-5-(benzyloxy)-3-hydroxy-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: 93.0%

(-)-(R)-4-benzyl-3-[(2R,3S)-5-(benzyloxy)-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one (870091-89-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (179945-11-0)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In n-heptane; dichloromethane; at 0 - 20 ℃;

(-)-(R)-4-benzyl-3-[(2R,3S)-5-(benzyloxy)-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one; In n-heptane; dichloromethane; at -15 - 0 ℃;

DOI:10.1016/j.tet.2010.06.074

Reference yield:

(4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (157220-39-8) → (2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (179945-11-0)

Guidance literature:

With Me₂AlN(Me)OMe; In tetrahydrofuran; at -10 - 0 ℃;

DOI:10.1016/0040-4039(94)88035-2

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (179945-11-0)

Guidance literature:

Multi-step reaction with 2 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

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Evans syn-selective aldol reaction;

DOI:10.1002/ejoc.200500206

upstream raw materials:

(4R,5S)-3-((2R,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

N,O-dimethylhydroxylamine*hydrochloride

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

3-Benzyloxypropanal

Downstream raw materials:

(2R,3S)-5-Benzyloxy-2-methyl-3-triethylsilanyloxy-pentanoic acid methoxy-methyl-amide

(2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide

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

(3R,5S,7S,8R)-3-(benzyloxy)-7-[2-(benzyloxy)ethyl]-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-9-one