(2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane

Base Information

• Chemical Name: (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane
• CAS No.: 146500-06-3
• Molecular Formula: C₃₇H₅₂N₂O₅Si
• Molecular Weight: 632.916
• Mol file: 146500-06-3.mol

Synonyms:(2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane

Chemical Property of (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane

There total 8 articles about (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane 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:

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate (133333-27-4) → (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane (146500-06-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, -78 deg C, 30 min

2: 1.) lithium diisopropylamide / 1.) hexane, THF, -78 to -55 deg C, 1 h, 2.a) THF, HMPA, -78 deg C, 30 min, b) -40 deg C, 2 h

3: 1.) aq. NaHCO₃, m-chloroperbenzoic acid, 2.) H₂ / 2.) 10percent Pd/C / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) ethyl acetate, methanol, 1 h

4: aq. LiOH / 1,2-dimethoxy-ethane / 12 h / 23 °C

5: imidazole / dimethylformamide / 12 h / 23 °C

6: 1.) diphenyl phosphorazidate, Et₃N / 1.) toluene, reflux, 1 h, 2.) reflux, 12 h

With 1H-imidazole; lithium hydroxide; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00057a011

Reference yield:

iodomethylbenzene (620-05-3) → (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane (146500-06-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, -78 deg C, 30 min

2: 1.) lithium diisopropylamide / 1.) hexane, THF, -78 to -55 deg C, 1 h, 2.a) THF, HMPA, -78 deg C, 30 min, b) -40 deg C, 2 h

3: 1.) aq. NaHCO₃, m-chloroperbenzoic acid, 2.) H₂ / 2.) 10percent Pd/C / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) ethyl acetate, methanol, 1 h

4: aq. LiOH / 1,2-dimethoxy-ethane / 12 h / 23 °C

5: imidazole / dimethylformamide / 12 h / 23 °C

6: 1.) diphenyl phosphorazidate, Et₃N / 1.) toluene, reflux, 1 h, 2.) reflux, 12 h

With 1H-imidazole; lithium hydroxide; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00057a011

Reference yield:

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one (98818-41-8) → (2S,4S,5S)-2-<<(phenylmethoxy)carbonyl>amino>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(1,1-dimethylethoxy)carbonyl>amino>-1,6-diphenylhexane (146500-06-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium diisopropylamide / 1.) hexane, THF, -78 to -55 deg C, 1 h, 2.a) THF, HMPA, -78 deg C, 30 min, b) -40 deg C, 2 h

2: 1.) aq. NaHCO₃, m-chloroperbenzoic acid, 2.) H₂ / 2.) 10percent Pd/C / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) ethyl acetate, methanol, 1 h

3: aq. LiOH / 1,2-dimethoxy-ethane / 12 h / 23 °C

4: imidazole / dimethylformamide / 12 h / 23 °C

5: 1.) diphenyl phosphorazidate, Et₃N / 1.) toluene, reflux, 1 h, 2.) reflux, 12 h

With 1H-imidazole; lithium hydroxide; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00057a011

upstream raw materials:

(2S,4S,5S)-5-{[(1,1-dimethylethoxy)carbonyl]amino}-4-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-6-phenyl-2-(phenylmethyl)hexanoic acid

benzyl alcohol

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

Downstream raw materials:

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

((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester

((1S,3S,4S)-4-Amino-1-benzyl-3-hydroxy-5-phenyl-pentyl)-carbamic acid benzyl ester

di(tert-butyl) N,N'-((2S,5S)-3-oxo-1,6-diphenylhexane-2,5-diyl)dicarbamate