2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester

Base Information

• Chemical Name: 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester
• CAS No.: 196868-19-6
• Molecular Formula: C₁₇H₂₄N₂O₅
• Molecular Weight: 336.388
• Mol file: 196868-19-6.mol

Synonyms:2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester

Chemical Property of 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester

There total 5 articles about 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester 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%

2-[((2R,3R,4R)-3-Acetylamino-4,5-dihydroxy-tetrahydro-furan-2-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester → 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester (196868-19-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 25h; under 2378.9 Torr; Ambient temperature;

DOI:10.1021/jo9708497

Reference yield:

2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester (196868-11-8) → 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester (196868-19-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / aq. Na₂CO₃ / dioxane / 17 h / Ambient temperature

2: NaBH₄ / Pd/C / methanol; H₂O / 0.75 h / Ambient temperature

3: pyridine / 17 h / Ambient temperature

4: 70 percent / TFA, water / 21 h / 0 - 4 °C

5: 81 percent / H₂ / Pd/C / methanol / 25 h / 2378.9 Torr / Ambient temperature

With pyridine; sodium tetrahydroborate; water; hydrogen; sodium carbonate; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; water;

DOI:10.1021/jo9708497

Reference yield:

2-[((3aR,5R,6S,6aR)-6-Amino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester → 2-((3R,4R,5S)-4-Acetylamino-3,5-dihydroxy-piperidin-1-yl)-3-phenyl-propionic acid methyl ester (196868-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 17 h / Ambient temperature

2: 70 percent / TFA, water / 21 h / 0 - 4 °C

3: 81 percent / H₂ / Pd/C / methanol / 25 h / 2378.9 Torr / Ambient temperature

With pyridine; water; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol;

DOI:10.1021/jo9708497

upstream raw materials:

2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-amino]-3-phenyl-propionic acid methyl ester

2-[((3aR,5R,6S,6aR)-6-Acetylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester

2-[((3aR,5R,6S,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl)-benzyloxycarbonyl-amino]-3-phenyl-propionic acid methyl ester