(-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

Base Information

Chemical Name:(-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone
CAS No.:117097-30-0
Molecular Formula:C₁₈H₂₂N₂O₆
Molecular Weight:362.382
Hs Code.:

Synonyms:(-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

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Chemical Property of (-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

Chemical Property:

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Technology Process of (-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

There total 12 articles about (-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone 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: 99.0%

: 117097-29-7
(-)-(2S,3R,4S,5S)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-3,4,5-piperidinetriol

: 117097-30-0
(-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

Guidance literature:: With ruthenium tetroxide; In tetrachloromethane; dichloromethane;
DOI:10.1021/ja00229a069

Reference yield:

: 117097-24-2
5-azido-5-deoxy-2,3-O-isopropylidene-L-ribono-1,4-lactone

: 117097-30-0
(-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / H₂ / Raney Ni / methanol

2: 1.) imidazole, 2.) NaH / DMF

3: 70 percent / NaBH₄ / ethanol

4: 88 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

5: Ph₃P, DEAD / dimethylformamide

7: 99 percent / RuO₄ / CH₂Cl₂; CCl₄

With 1H-imidazole; sodium tetrahydroborate; ruthenium tetroxide; oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; nickel; In methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00229a069

Reference yield:

: 41546-21-8
L-ribose

: 117097-30-0
(-)-(4R,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone

Guidance literature:: Multi-step reaction with 8 steps

2: 88 percent / H₂ / Raney Ni / methanol

3: 1.) imidazole, 2.) NaH / DMF

4: 70 percent / NaBH₄ / ethanol

5: 88 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

6: Ph₃P, DEAD / dimethylformamide

8: 99 percent / RuO₄ / CH₂Cl₂; CCl₄

With 1H-imidazole; sodium tetrahydroborate; ruthenium tetroxide; oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; nickel; In methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00229a069