N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal

Base Information

• Chemical Name: N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal
• CAS No.: 142545-25-3
• Molecular Formula: C₂₃H₂₉NO₄
• Molecular Weight: 383.488
• Mol file: 142545-25-3.mol

Synonyms:N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal

Chemical Property of N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal

There total 8 articles about N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal 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: 95.0%

Benzyl-((S)-3-benzyloxy-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester (142545-28-6) → N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal (142545-25-3)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4020(01)92199-4

Reference yield:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) → N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal (142545-25-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / dicyclohexylcarbodiimide / 72 h / Ambient temperature

2: 94 percent / imidazole / dimethylformamide / 2 h / 40 °C

3: 98 percent / H₂ / 5percent Pd/C / methanol / 8 h / Ambient temperature

4: 82 percent / LiAlH₄ / diethyl ether / 1) -25 deg C, 2) 0 deg C, 2 h

5: 74 percent / NaH / dimethylformamide / 2 h / Ambient temperature

6: 97 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

7: 95 percent / SO₃-pyridine, Et₃N / dimethylsulfoxide / 0.25 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)92199-4

Reference yield:

methyl (3S)-3-[[(benzyloxy)carbonyl]amino]-4-hydroxybutanoate (192517-47-8) → N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal (142545-25-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / imidazole / dimethylformamide / 2 h / 40 °C

2: 98 percent / H₂ / 5percent Pd/C / methanol / 8 h / Ambient temperature

3: 82 percent / LiAlH₄ / diethyl ether / 1) -25 deg C, 2) 0 deg C, 2 h

4: 74 percent / NaH / dimethylformamide / 2 h / Ambient temperature

5: 97 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

6: 95 percent / SO₃-pyridine, Et₃N / dimethylsulfoxide / 0.25 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)92199-4

upstream raw materials:

Benzyl-((S)-3-benzyloxy-1-hydroxymethyl-propyl)-carbamic acid tert-butyl ester

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

benzyl bromide

(S)-3-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid methyl ester

Downstream raw materials:

Benzyl-[(1S,2S,3S)-1-(2-benzyloxy-ethyl)-2,3-dihydroxy-butyl]-carbamic acid tert-butyl ester

4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-1,2-2(S)-epoxy-3(S)-hydroxyhexane

4(S)-(N-Benzyl-N-tert-butyloxycarbonyl)amino-6-benzyloxy-2,3-(2S,3S)-isopropylidenedioxyhexane

4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1

Refernces