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

Base Information

• Chemical Name: (-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol
• CAS No.: 127181-15-1
• Molecular Formula: C₁₉H₂₆N₂O₆
• Molecular Weight: 378.425
• Mol file: 127181-15-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol 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%

(+)-(4R,5S,6R)-6-acetamido-N-(benzyloxycarbonyl)-2,3-didehydro-4,5-(isopropylidenedioxy)-3-piperidinecarboxylic acid methoxyethoxymethyl ester (127181-14-0) → (-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol (127181-15-1)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 3h; 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) → (-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol (127181-15-1)

Guidance literature:

Multi-step reaction with 18 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

17: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

18: 81 percent / NaBH₄ / tetrahydrofuran; various solvent(s) / 3 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; N-ethyl-N,N-diisopropylamine; 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:

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) → (-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol (127181-15-1)

Guidance literature:

Multi-step reaction with 19 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

18: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

19: 81 percent / NaBH₄ / tetrahydrofuran; various solvent(s) / 3 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; N-ethyl-N,N-diisopropylamine; 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

upstream raw materials:

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

2,3-O-isopropylidene-D-ribofuranose

D-Ribose

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

Downstream raw materials:

(3aS,4R,7R,7aR)-4-Acetylamino-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5,7-dicarboxylic acid 5-benzyl ester