(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

Base Information

Chemical Name:(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one
CAS No.:239784-28-2
Molecular Formula:C₂₂H₃₄N₂O₅
Molecular Weight:406.522
Hs Code.:

Synonyms:(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

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Chemical Property of (3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

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Technology Process of (3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

There total 13 articles about (3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one 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:

: 21691-53-2
L-leucine tert-butyl ester

: 239784-28-2
(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / 2,6-lutidine / CH₂Cl₂ / Heating

2: K₂CO₃ / acetonitrile / Heating

3: NaH / tetrahydrofuran

4: 70 percent / K₂CO₃, KI / acetonitrile / 32 h / Heating

5: 66 percent / PPTS / methanol / 24 h / Heating

6: 1.) Et₃N; 2.) SOCl₂ / 1.) THF, 0 deg C; 2.) 0 deg C, 1 h

7: 90 percent / NaN₃ / hexamethylphosphoric acid triamide / 15 h / Ambient temperature

8: H₂ / Pd/C/PbAcO₂ / ethanol / 24 h

With 2,6-dimethylpyridine; thionyl chloride; sodium azide; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(99)00897-7

Reference yield:

: 239784-31-7
(S)-2-[((3aR,4R,6aR)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl)-amino]-4-methyl-pentanoic acid tert-butyl ester

: 239784-28-2
(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / NaOAc / methanol / 48 h / Heating

2: 70 percent / K₂CO₃, KI / acetonitrile / 32 h / Heating

3: 66 percent / PPTS / methanol / 24 h / Heating

4: 1.) Et₃N; 2.) SOCl₂ / 1.) THF, 0 deg C; 2.) 0 deg C, 1 h

5: 90 percent / NaN₃ / hexamethylphosphoric acid triamide / 15 h / Ambient temperature

6: H₂ / Pd/C/PbAcO₂ / ethanol / 24 h

With thionyl chloride; sodium azide; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; potassium iodide; palladium on activated charcoal; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; acetonitrile;
DOI:10.1016/S0040-4039(99)00897-7

Reference yield:

: 239784-35-1
(S)-2-[((4R,5R)-2,2-Dimethyl-5-(R)-oxiranyl-[1,3]dioxolane-4-carbonyl)-amino]-4-methyl-pentanoic acid tert-butyl ester

: 239784-28-2
(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran

2: 70 percent / K₂CO₃, KI / acetonitrile / 32 h / Heating

3: 66 percent / PPTS / methanol / 24 h / Heating

4: 1.) Et₃N; 2.) SOCl₂ / 1.) THF, 0 deg C; 2.) 0 deg C, 1 h

5: 90 percent / NaN₃ / hexamethylphosphoric acid triamide / 15 h / Ambient temperature

6: H₂ / Pd/C/PbAcO₂ / ethanol / 24 h

With thionyl chloride; sodium azide; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; acetonitrile;
DOI:10.1016/S0040-4039(99)00897-7