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

Base Information

• Chemical Name: (3S,4S,5R)-3-azido-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one
• CAS No.: 239784-38-4
• Molecular Formula: C₂₂H₃₂N₄O₅
• Molecular Weight: 432.52
• Mol file: 239784-38-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (3S,4S,5R)-3-azido-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: 90.0%

(S)-2-((2R,3aR,7R,7aR)-7-Benzyloxy-2,4-dioxo-tetrahydro-1,3-dioxa-2λ4-thia-5-aza-inden-5-yl)-4-methyl-pentanoic acid tert-butyl ester → (3S,4S,5R)-3-azido-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one (239784-38-4)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 15h; Ambient temperature;

DOI:10.1016/S0040-4039(99)00897-7

Reference yield: 90.0%

(S)-2-((2S,3aR,7R,7aR)-7-Benzyloxy-2,4-dioxo-tetrahydro-1,3-dioxa-2λ4-thia-5-aza-inden-5-yl)-4-methyl-pentanoic acid tert-butyl ester → (3S,4S,5R)-3-azido-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one (239784-38-4)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 15h; Ambient temperature;

DOI:10.1016/S0040-4039(99)00897-7

Reference yield:

L-leucine tert-butyl ester (21691-53-2) → (3S,4S,5R)-3-azido-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one (239784-38-4)

Guidance literature:

Multi-step reaction with 7 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

With 2,6-dimethylpyridine; thionyl chloride; sodium azide; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; potassium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(99)00897-7

upstream raw materials:

2,3-O-isopropylidene-D-ribonic-γ-lactone

L-leucine tert-butyl ester

2,3-O-isopropylidene-5-iodo-D-ribono-1,4-lactone

5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone

Downstream raw materials:

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