(3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester

Base Information

• Chemical Name: (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester
• CAS No.: 189026-29-7
• Molecular Formula: C₁₇H₂₃N₃O₈
• Molecular Weight: 397.385
• Mol file: 189026-29-7.mol

Synonyms:

Chemical Property of (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester

There total 10 articles about (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl 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: 97.0%

(2S,3S)-3-Acetoxy-2-[N-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-N'-tert-butoxycarbonyl-hydrazino]-4-[1,3]dioxolan-2-yl-butyric acid isobutyl ester (189026-28-6) → (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester (189026-29-7)

Guidance literature:

With tetrahydrofuran; In water; for 0.5h;

DOI:10.1021/jo9701952

Reference yield:

(S)-4-[1,3]Dioxolan-2-yl-3-hydroxy-butyric acid isobutyl ester (189026-24-2) → (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester (189026-29-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 61 percent / LDA / tetrahydrofuran / -78 °C

2: 95 percent / pyridine / 16 h / Ambient temperature

3: 97 percent / H₂ / Pd/C / 8 h / Ambient temperature

4: 60 percent / sym-collidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 97 percent / THF / H₂O / 0.5 h

With tetrahydrofuran; 2,4,6-trimethyl-pyridine; hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water;

DOI:10.1021/jo9701952

Reference yield:

(S)-5-Oxo-3-tributylsilanyloxy-pentanoic acid isobutyl ester → (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester (189026-29-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / PPTS / benzene / 3 h / Heating

2: 85 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature

3: 61 percent / LDA / tetrahydrofuran / -78 °C

4: 95 percent / pyridine / 16 h / Ambient temperature

5: 97 percent / H₂ / Pd/C / 8 h / Ambient temperature

6: 60 percent / sym-collidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 97 percent / THF / H₂O / 0.5 h

With tetrahydrofuran; 2,4,6-trimethyl-pyridine; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water; benzene;

DOI:10.1021/jo9701952

upstream raw materials:

(2S,3S)-3-Acetoxy-2-[N-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-N'-tert-butoxycarbonyl-hydrazino]-4-[1,3]dioxolan-2-yl-butyric acid isobutyl ester

(S)-4-[1,3]Dioxolan-2-yl-3-hydroxy-butyric acid isobutyl ester

isobutyl (3S)-5-benzyloxy-3-hydroxypentanoate

(2S,3S)-3-Acetoxy-2-(N'-tert-butoxycarbonyl-hydrazino)-4-[1,3]dioxolan-2-yl-butyric acid isobutyl ester