(2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Base Information

• Chemical Name: (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid
• CAS No.: 98737-45-2
• Molecular Formula: C₃₀H₄₅NO₅Si
• Molecular Weight: 527.777
• Mol file: 98737-45-2.mol

Synonyms:(2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Chemical Property of (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

There total 10 articles about (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic 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: 91.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,4R,5S)-2-Benzyl-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenylhexanoic acid (98737-43-0) → (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid (98737-45-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 96h; Ambient temperature;

DOI:10.1135/cccc19980541

Reference yield:

(4R,5R)-5-hydroxy-6-phenyl-4-hexanolide (125225-54-9) → (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid (98737-45-2)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP, Et₃N / CH₂Cl₂ / 0 °C

2: 87 percent / NaN₃ / dimethylformamide / 90 °C

3: H₂ / 10 percent Pd/C / ethyl acetate

4: ethyl acetate / 23 °C

5: 70 percent / LiHMDS / tetrahydrofuran / -78 °C

6: LiOH, H₂O / 1,2-dimethoxy-ethane / 23 °C

7: imidazole / dimethylformamide / 23 °C

With 1H-imidazole; dmap; lithium hydroxide; sodium azide; water; hydrogen; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/a902518i

Reference yield:

Methanesulfonic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl ester (145761-24-6) → (2S,4R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid (98737-45-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / NaN₃ / dimethylformamide / 90 °C

2: H₂ / 10 percent Pd/C / ethyl acetate

3: ethyl acetate / 23 °C

4: 70 percent / LiHMDS / tetrahydrofuran / -78 °C

5: LiOH, H₂O / 1,2-dimethoxy-ethane / 23 °C

6: imidazole / dimethylformamide / 23 °C

With 1H-imidazole; lithium hydroxide; sodium azide; water; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/a902518i

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,4R,5S)-2-Benzyl-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenylhexanoic acid

(4R,5R)-5-hydroxy-6-phenyl-4-hexanolide

Methanesulfonic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl ester

Downstream raw materials:

tert-butyl (1S,2R,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentylcarbamate

(2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane

(2S,4S,5S)-2,5-bis<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenyl-4-hydroxyhexane