9-Oxa-2,5-diaza-10-siladodecanoic acid, 6-amino-11,11-dimethyl-4-oxo-10,10-diphenyl-3-(phenylmethyl)-, phenylmethyl ester, (3S,6R)-

Base Information

• Chemical Name: 9-Oxa-2,5-diaza-10-siladodecanoic acid, 6-amino-11,11-dimethyl-4-oxo-10,10-diphenyl-3-(phenylmethyl)-, phenylmethyl ester, (3S,6R)-
• CAS No.: 928406-71-7
• Molecular Formula: C36H43N3O4Si
• Molecular Weight: 609.841
• Mol file: 928406-71-7.mol

Synonyms:

Chemical Property of 9-Oxa-2,5-diaza-10-siladodecanoic acid, 6-amino-11,11-dimethyl-4-oxo-10,10-diphenyl-3-(phenylmethyl)-, phenylmethyl ester, (3S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-Oxa-2,5-diaza-10-siladodecanoic acid, 6-amino-11,11-dimethyl-4-oxo-10,10-diphenyl-3-(phenylmethyl)-, phenylmethyl ester, (3S,6R)-

There total 4 articles about 9-Oxa-2,5-diaza-10-siladodecanoic acid, 6-amino-11,11-dimethyl-4-oxo-10,10-diphenyl-3-(phenylmethyl)-, phenylmethyl ester, (3S,6R)- 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: 78.0%

{(S)-1-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carbamoyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (928406-70-6) → {(S)-1-[(R)-1-Amino-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (928406-71-7)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃;

DOI:10.1016/j.bmcl.2006.10.017

Reference yield:

(R)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-4-hydroxy-butyric acid (928406-68-2) → {(S)-1-[(R)-1-Amino-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (928406-71-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HOBt; EDC / tetrahydrofuran / 20 °C

1.2: aq. NH₃ / tetrahydrofuran

2.1: 93 percent / imidazole / dimethylformamide / 20 °C

3.1: 78 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H₂O / 20 °C

With 1H-imidazole; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Hofmann rearrangement;

DOI:10.1016/j.bmcl.2006.10.017

Reference yield:

[(S)-1-((R)-1-Carbamoyl-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (928406-69-3) → {(S)-1-[(R)-1-Amino-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (928406-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / imidazole / dimethylformamide / 20 °C

2: 78 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H₂O / 20 °C

With 1H-imidazole; bis-[(trifluoroacetoxy)iodo]benzene; In water; N,N-dimethyl-formamide; acetonitrile; 2: Hofmann rearrangement;

DOI:10.1016/j.bmcl.2006.10.017

upstream raw materials:

{(S)-1-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carbamoyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester

[(S)-1-((R)-1-Carbamoyl-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

(R)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-4-hydroxy-butyric acid

N-Cbz-L-Phe

Downstream raw materials:

[(S)-1-((R)-1-Amino-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate

((S)-1-{(2R,4S)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

((S)-1-{(2S,4S)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

Refernces