2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane

Base Information

• Chemical Name: 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane
• CAS No.: 326480-02-8
• Molecular Formula: C₂₁H₃₆ClNO₃Si
• Molecular Weight: 414.06
• Mol file: 326480-02-8.mol

Synonyms:2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane

Chemical Property of 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane

There total 4 articles about 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane 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: 75.0%

phenylmagnesium chloride (100-59-4) + N-t-butyloxycarbonyl-2(S)-(1(S)-t-butyldimethylsilyloxy-2-chloroethyl)aziridine (326480-01-7) → 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane (326480-02-8)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; toluene; at -78 - -20 ℃;

DOI:10.1021/ol016147s

Reference yield: 75.0%

→ 2(S)-t-butyldimetylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane + 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane (326480-02-8)

Guidance literature:

Reference yield:

2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane (326479-99-6) → 2(S)-t-butyldimethylsilyloxy-3(S)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane (326480-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / imidazole; DMAP / dimethylformamide / 12 h / 50 °C

2: 100 percent / NaH / tetrahydrofuran / 5 h / 0 °C

3: 75 percent / CuBr*Me₂S / toluene; tetrahydrofuran / -78 - -20 °C

With 1H-imidazole; dmap; copper(I) bromide dimethylsulfide complex; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol016147s

upstream raw materials:

phenylmagnesium chloride

N-t-butyloxycarbonyl-2(S)-(1(S)-t-butyldimethylsilyloxy-2-chloroethyl)aziridine

2(R)-((tert-butyloxycarbonyl)amino)-1,4-dichloro-3(S)-hydroxybutane

2(S)-t-butyldimethylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1,4-dichlorobutane

Downstream raw materials:

4-nitro-N-((2R(syn),3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutylbenzenesulfonamide

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

amprenavir

(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol