(2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid

Base Information

• Chemical Name: (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid
• CAS No.: 869494-32-6
• Molecular Formula: C₂₆H₄₅NO₅Si
• Molecular Weight: 479.733
• Mol file: 869494-32-6.mol

Synonyms:(2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid

Chemical Property of (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid

There total 7 articles about (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid 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: 55.0%

tert-butyl N-[(1S)-1-[(2S,4R)-4-benzyl-5-oxooxolan-2-yl]-2-methylpropyl]carbamate + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid (869494-32-6)

Guidance literature:

tert-butyl N-[(1S)-1-[(2S,4R)-4-benzyl-5-oxooxolan-2-yl]-2-methylpropyl]carbamate; With lithium hydroxide monohydrate; In tetrahydrofuran; water; for 1.16667h;

With 1-methyl-1H-imidazole; iodine; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

tert-butyldimethylsilyl chloride; Further stages;

DOI:10.1002/chem.202102204

Reference yield:

tert-butyl (3S,4RS)-6-(ethoxycarbonyl)-4-hydroxy-2-methylhex-5-yn-3-ylcarbamate → (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid (869494-32-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd(OH)2/C / ethyl acetate / 12 h

2.1: 772 mg / AcOH / toluene / 12 h / Heating

3.1: LDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 55 percent / hexane; tetrahydrofuran / 1.67 h / -78 °C

4.1: aq. LiOH / tetrahydrofuran / 0.67 h / 20 °C

5.1: 191 mg / imidazole / dimethylformamide / 24 h / 23 °C

With 1H-imidazole; lithium hydroxide; hydrogen; acetic acid; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm050548m

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid (869494-47-3) → (2R,4S,5S)-2-benzyl-5-{[(tert-butoxy)carbonyl]amino}-4-[(tertbutyldimethylsilyl)oxy]-6-methylheptanoic acid (869494-32-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 24h;

DOI:10.1021/jm050548m

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-hydroxy-6-methyl-heptanoic acid

tert-butyl (S)-1-((2S,4R)-4-benzyltetrahydro-5-oxofuran-2-yl)-2-methylpropylcarbamate

tert-butyl ((S)-2-methyl-1-((R)-5-oxotetrahydrofuran-2-yl)propyl)carbamate

Downstream raw materials:

(E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

(E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

(E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-hydroxy-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester