(2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

Base Information

• Chemical Name: (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole
• CAS No.: 316824-52-9
• Molecular Formula: C₁₇H₁₉NO₇
• Molecular Weight: 349.34
• Mol file: 316824-52-9.mol

Synonyms:(2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

Chemical Property of (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole

There total 5 articles about (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole 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: 56.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + (3R)-3-benzyloxy-1-pyrroline 1-oxide (217173-97-2) → (2R,3S,3aR,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole + (2R,3S,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole + (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole (316824-52-9)

Guidance literature:

In benzene; for 72h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1055/s-1997-3222

Reference yield:

(2R)-2-benzyloxy-1,4-bis(methanesulfonyloxy)butane (217173-96-1) → (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole (316824-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₂OH*HCl; triethylamine / 2 h / Heating

2: HgO / CH₂Cl₂ / 4 h / 20 °C

3: 56 percent / benzene / 72 h / 20 °C

With hydroxylamine hydrochloride; triethylamine; mercury(II) oxide; In dichloromethane; benzene; 1: Substitution / 2: Oxidation / 3: Cycloaddition;

Reference yield:

Benzoic acid (R)-1-hydroxy-pyrrolidin-3-yl ester → (2S,3R,3aS,4R)-4-benzoyloxy-2,3-bis(methoxycarbonyl)hexahydropyrrolo[1,2-b]isoxazole (316824-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: HgO / CH₂Cl₂ / 4 h / 20 °C

2: 56 percent / benzene / 72 h / 20 °C

With mercury(II) oxide; In dichloromethane; benzene; 1: Oxidation / 2: Cycloaddition;

upstream raw materials:

dimethyl cis-but-2-ene-1,4-dioate

(3R)-3-benzyloxy-1-pyrroline 1-oxide

benzoic acid

(2R)-2-benzyloxy-1,4-bis(methanesulfonyloxy)butane

Downstream raw materials:

(-)-(1S,6R,6aS,7R)-6-(Benzoyloxy)-7-carbomethoxy-1-hydroxyhexahydro-1H-pyrrolizin-2-one