(3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine

Base Information

• Chemical Name: (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine
• CAS No.: 320574-51-4
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 320574-51-4.mol

Synonyms:(3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine

Chemical Property of (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine

There total 4 articles about (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine 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:

Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate (121614-07-1) → (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine (320574-51-4)

Guidance literature:

Multi-step reaction with 4 steps

1: HF; pyridine / 0.5 h / 0 °C

2: NaOMe / methanol / 4 h / 20 °C

3: DIBAH / CH₂Cl₂ / 1 h / -80 °C

4: pyridine / 0.5 h / 0 °C

With pyridine; hydrogen fluoride; sodium methylate; diisobutylaluminium hydride; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)01674-9

Reference yield:

(3S,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one (204577-42-4) → (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine (320574-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAH / CH₂Cl₂ / 1 h / -80 °C

2: pyridine / 0.5 h / 0 °C

With pyridine; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1016/S0040-4039(00)01674-9

Reference yield:

(S)-3-(Benzyl-hydroxy-amino)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester (425427-09-4) → (3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine (320574-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol / 4 h / 20 °C

2: DIBAH / CH₂Cl₂ / 1 h / -80 °C

3: pyridine / 0.5 h / 0 °C

With pyridine; sodium methylate; diisobutylaluminium hydride; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)01674-9

upstream raw materials:

acetic anhydride

Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate

(3S,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one

(S)-3-(Benzyl-hydroxy-amino)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester

Downstream raw materials:

1-{(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine

1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine

1-[(3S,5R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-yl]-1H-pyrimidine-2,4-dione

1-[(3S,5S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-yl]-1H-pyrimidine-2,4-dione