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

Base Information

• Chemical Name: (+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone
• CAS No.: 127181-13-9
• Molecular Formula: C₁₈H₂₂N₂O₆
• Molecular Weight: 362.382
• Mol file: 127181-13-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (+)-(4S,5S,6R)-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: 98.0%

(+)-(2R,3S,4R,5R)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-3,4,5-piperidinetriol (127181-11-7) → (+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone (127181-13-9)

Guidance literature:

With ruthenium tetroxide; In tetrachloromethane; dichloromethane; for 1h; Ambient temperature;

DOI:10.1246/bcsj.65.978

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone (127181-13-9)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine / -30 °C

2: NaN₃ / dimethylsulfoxide / 2 h / 65 °C

3: pyridine, CrO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

4: H₂ / Raney Ni / methanol / 2 h / Ambient temperature

5: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

6: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

7: 92 percent / sodium borohydride / ethanol / Ambient temperature

8: 1) dimethyl sulfoxide, oxalyl dichloride; 3) triethylamine / 1) CH₂Cl₂, -60 deg C, 5 min; 2) CH₂Cl₂, -60 deg C, 15 min; 3) CH₂Cl₂, -60 deg C, 10 min, then room temp.

9: 98 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

10: 1.) hydrazine, 2.) pyridine / 1.) methanol, 30 deg C, 1 d, 2.) RT, overnight

11: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

12: 98 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; sodium azide; ruthenium tetroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.978

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (+)-(4S,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-4,5-(isopropylidenedioxy)-3-piperidinone (127181-13-9)

Guidance literature:

Multi-step reaction with 13 steps

1: p-toluenesulfonic acid monohydrate / a) 10 deg C, 1h, b) RT, 3 h

2: pyridine / -30 °C

3: NaN₃ / dimethylsulfoxide / 2 h / 65 °C

4: pyridine, CrO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

5: H₂ / Raney Ni / methanol / 2 h / Ambient temperature

6: 93 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

7: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

8: 92 percent / sodium borohydride / ethanol / Ambient temperature

9: 1) dimethyl sulfoxide, oxalyl dichloride; 3) triethylamine / 1) CH₂Cl₂, -60 deg C, 5 min; 2) CH₂Cl₂, -60 deg C, 15 min; 3) CH₂Cl₂, -60 deg C, 10 min, then room temp.

10: 98 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

11: 1.) hydrazine, 2.) pyridine / 1.) methanol, 30 deg C, 1 d, 2.) RT, overnight

12: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

13: 98 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; sodium azide; ruthenium tetroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.978

upstream raw materials:

(+)-(2R,3S,4R,5R)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-3,4,5-piperidinetriol

2,3-O-isopropylidene-D-ribofuranose

D-Ribose

5-amino-5-deoxy-2,3-O-isopropylidene-D-ribono-1,5-lactam

Downstream raw materials:

(-)-(2R,3S,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-3,4-O-isopropylidene-5-(nitromethyl)-3,4,5-piperidinetriol

(-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol

(3aS,4R,7aR)-4-Acetylamino-7-formyl-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid benzyl ester

(+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid