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

Base Information

Chemical Name:(+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid
CAS No.:141781-99-9
Molecular Formula:C₁₉H₂₂N₂O₇
Molecular Weight:390.393
Hs Code.:

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

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

There total 17 articles about (+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid 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:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 141781-99-9
(+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid

Guidance literature:: Multi-step reaction with 16 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

13: 100 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

14: 1.) acetic anhydride, p-toluenesulfonic acid, 2.) K₂CO₃ / 1.) RT, overnight, 2.) benzene, RT, overnight

15: pyridine / 168 h / 38 °C

16: aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 24 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; sodium azide; ruthenium tetroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1246/bcsj.65.978

Reference yield:

: 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
D-Ribose

: 141781-99-9
(+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid

Guidance literature:: Multi-step reaction with 17 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

14: 100 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

15: 1.) acetic anhydride, p-toluenesulfonic acid, 2.) K₂CO₃ / 1.) RT, overnight, 2.) benzene, RT, overnight

16: pyridine / 168 h / 38 °C

17: aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 24 h / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; sodium azide; ruthenium tetroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1246/bcsj.65.978

Reference yield:

: 23709-18-4
(3aR,6R,6aR)-6-(azidomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

: 141781-99-9
(+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid

Guidance literature:: Multi-step reaction with 13 steps

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

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

3: 96 percent / NaH / dimethylformamide / 2 h / Ambient temperature

4: 92 percent / sodium borohydride / ethanol / Ambient temperature

5: 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.

6: 98 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

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

8: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

9: 98 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

10: 100 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

11: 1.) acetic anhydride, p-toluenesulfonic acid, 2.) K₂CO₃ / 1.) RT, overnight, 2.) benzene, RT, overnight

12: pyridine / 168 h / 38 °C

13: aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 24 h / Ambient temperature

With pyridine; 1H-imidazole; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; ruthenium tetroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1246/bcsj.65.978