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

Base Information

• Chemical Name: (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid
• CAS No.: 125165-38-0
• Molecular Formula: C₁₉H₂₂N₂O₇
• Molecular Weight: 390.393

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (-)-(4S,5R,6S)-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:

5-azido-5-deoxy-2,3-O-isopropylidene-L-ribono-1,4-lactone (117097-24-2) → (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid (125165-38-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 87.7 percent / H₂ / Raney Ni / methanol / 2 h / Ambient temperature

2: 98 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

3: 98 percent / NaH / dimethylformamide / 2 h / Ambient temperature

4: 96 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: 100 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

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

8: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

9: 99 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

10: 99.6 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

Reference yield:

5-azido-5-deoxy-2,3-O-isopropylidene-L-ribofuranose → (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid (125165-38-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 96.6 percent / pyridine, CrO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 87.7 percent / H₂ / Raney Ni / methanol / 2 h / Ambient temperature

3: 98 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

4: 98 percent / NaH / dimethylformamide / 2 h / Ambient temperature

5: 96 percent / sodium borohydride / ethanol / Ambient temperature

6: 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.

7: 100 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

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

9: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

10: 99 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

11: 99.6 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

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

13: pyridine / 168 h / 38 °C

14: 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; 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

Reference yield:

5-amino-5-deoxy-2,3-O-isopropylidene-L-1,5-ribonolactam (117179-01-8) → (-)-(4S,5R,6S)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid (125165-38-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 98 percent / NaH / dimethylformamide / 2 h / Ambient temperature

3: 96 percent / sodium borohydride / ethanol / Ambient temperature

4: 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.

5: 100 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature

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

7: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

8: 99 percent / RuO₄ / CCl₄; CH₂Cl₂ / 1 h / Ambient temperature

9: 99.6 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

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

11: pyridine / 168 h / 38 °C

12: 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; acetic anhydride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1246/bcsj.65.978

upstream raw materials:

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

5-amino-5-deoxy-2,3-O-isopropylidene-L-1,5-ribonolactam

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

5-amino-4-O-(t-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-L-1,5-ribonolactam

Downstream raw materials:

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

siastatin B

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

N-(benzyloxycarbonyl)-4,5-O-isopropylidenesiastatin B

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