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

Base Information

• Chemical Name: (3aS,4R,7R,7aR)-4-Acetylamino-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5,7-dicarboxylic acid 5-benzyl ester
• CAS No.: 127106-58-5
• Molecular Formula: C₁₉H₂₄N₂O₇
• Molecular Weight: 392.409

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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

There total 37 articles about (3aS,4R,7R,7aR)-4-Acetylamino-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5,7-dicarboxylic acid 5-benzyl ester 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: 75.0%

(+)-(2S,3R,4S,5R)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol (117097-34-4) → N-(benzyloxycarbonyl)-4,5-O-isopropylidenesiastatin B (127106-58-5,141781-91-1)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1246/bcsj.65.978

Reference yield: 70.0%

(-)-(2R,3S,4R,5S)-2-acetamido-N-(benzyloxycarbonyl)-5-(hydroxymethyl)-3,4-O-isopropylidene-3,4-piperidinediol (127181-15-1) → (3aS,4R,7R,7aR)-4-Acetylamino-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5,7-dicarboxylic acid 5-benzyl ester (127106-58-5)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; 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) → (3aS,4R,7R,7aR)-4-Acetylamino-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5,7-dicarboxylic acid 5-benzyl ester (127106-58-5)

Guidance literature:

Multi-step reaction with 19 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

19: 70 percent / pyridinium dichromate / dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; dipyridinium dichromate; 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:

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

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:

siastatin B

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