allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate

Base Information

• Chemical Name: allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate
• CAS No.: 511546-66-0
• Molecular Formula: C₂₁H₃₃NO₅Si
• Molecular Weight: 407.582
• Mol file: 511546-66-0.mol

Synonyms:allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate

Chemical Property of allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate

There total 3 articles about allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate 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: 85.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-2-Benzyloxycarbonylamino-4-hydroxy-butyric acid allyl ester (511546-59-1) → allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate (511546-66-0)

Guidance literature:

With pyridine; at 0 ℃; for 4h;

DOI:10.1021/jo026776v

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate (511546-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / aq. NaHCO₃ / 24 h / 20 °C

2.1: NaOH / H₂O; ethanol / 24 h / 20 °C

2.2: 96 percent / dimethylformamide / 48 h / 20 °C

3.1: 85 percent / pyridine / 4 h / 0 °C

With pyridine; sodium hydroxide; sodium hydrogencarbonate; In ethanol; water;

DOI:10.1021/jo026776v

Reference yield:

N-benzyloxycarbonyl-(L)-homoserine (35677-88-4) → allyl (2S)-2-(benzyloxycarbonyl)amino-4-[(tert-butyldimethylsilyl)oxy]butanoate (511546-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaOH / H₂O; ethanol / 24 h / 20 °C

1.2: 96 percent / dimethylformamide / 48 h / 20 °C

2.1: 85 percent / pyridine / 4 h / 0 °C

With pyridine; sodium hydroxide; In ethanol; water;

DOI:10.1021/jo026776v

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-2-Benzyloxycarbonylamino-4-hydroxy-butyric acid allyl ester

benzyl chloroformate

N-benzyloxycarbonyl-(L)-homoserine

Downstream raw materials:

[(S)-3-Oxo-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid benzyl ester

2S-2-(benzyloxycarbonyl)amino-1-(tetrahydro-2H-pyran-2-yloxy)-4-butanol

[3-(tert-butyl-dimethyl-silanyloxy)-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid benzyl ester

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{4-[4-acetyl-2S-(benzyloxycarbonyl)amino-1-butanol]}-D-erythro-L-manno-nonanoate