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

Base Information

Chemical Name:4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1
CAS No.:142545-24-2
Molecular Formula:C₂₅H₃₃NO₄
Molecular Weight:411.541
Hs Code.:

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

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

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

There total 9 articles about 4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1 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: 81.0%

: 3536-96-7
vinylmagnesium chloride

: 142545-25-3
N-Benzyl-N-tert-butyloxycarbonyl-O-benzyl-L-homoserinal

: 142545-24-2
4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1

Guidance literature:: In diethyl ether; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(01)92199-4

Reference yield:

: 87219-29-2
benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

: 142545-24-2
4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1

Guidance literature:: Multi-step reaction with 8 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

8: 81 percent / diethyl ether / 1 h / -78 °C

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:

: 192517-47-8
methyl (3S)-3-[[(benzyloxy)carbonyl]amino]-4-hydroxybutanoate

: 142545-24-2
4(S)-(N-Benzyl-N-tert-butoxycarbonyl)amino-6-benzyloxy-3(R)-hydroxyhexene-1

Guidance literature:: Multi-step reaction with 7 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

7: 81 percent / diethyl ether / 1 h / -78 °C

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