(2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole

Base Information

• Chemical Name: (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole
• CAS No.: 740805-29-2
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 740805-29-2.mol

Synonyms:(2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole

Chemical Property of (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole

There total 13 articles about (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[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: 85.0%

vinyl phenyl ether (766-94-9) + (3S,4R,5S)-3,4-isopropylidenedioxy-5-methyl-1-pyrroline-N-oxide (740805-26-9) → (3aS,3bS,5R,7S,7aR)-2,2,7-Trimethyl-5-phenoxy-hexahydro-1,3,6-trioxa-6a-aza-cyclopenta[a]pentalene + (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole (740805-29-2)

Guidance literature:

In 1,1,2,2-tetrachloroethylene; at 50 ℃;

DOI:10.1016/j.tetlet.2004.05.075

Reference yield:

benzyl 2,3-O-isopropylidene-D-ribofuranoside (23276-32-6) → (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole (740805-29-2)

Guidance literature:

Multi-step reaction with 8 steps

1: NEt₃

2: AlLiH₄ / diethyl ether

3: 96 percent / hydrogen / Pd/C

4: 96 percent / NH₂OH

5: 67 percent / pyridine

6: NEt₃

7: NBu₄F; CsF / 20 °C

8: 85 percent / tetrachloroethene / 50 °C

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; hydroxylamine; triethylamine; cesium fluoride; palladium on activated charcoal; In 1,1,2,2-tetrachloroethylene; diethyl ether;

DOI:10.1016/j.tetlet.2004.05.075

Reference yield:

benzyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (75100-21-9) → (2S,3aS,4S,5R,6S)-4,5-isopropylidenedioxy-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole (740805-29-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / hydrogen / Pd/C

2: 96 percent / NH₂OH

3: 67 percent / pyridine

4: NEt₃

5: NBu₄F; CsF / 20 °C

6: 85 percent / tetrachloroethene / 50 °C

With pyridine; tetrabutyl ammonium fluoride; hydrogen; hydroxylamine; triethylamine; cesium fluoride; palladium on activated charcoal; In 1,1,2,2-tetrachloroethylene;

DOI:10.1016/j.tetlet.2004.05.075

upstream raw materials:

vinyl phenyl ether

(3S,4R,5S)-3,4-isopropylidenedioxy-5-methyl-1-pyrroline-N-oxide

benzyl 2,3-O-isopropylidene-D-ribofuranoside

benzyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

Downstream raw materials:

(2S,3aS,4S,5R,6S)-6-methyl-2-phenoxyhexahydropyrrolo[1,2-b]isoxazole-4,5-diol

2-((3aS,4S,6S,6aR)-5-Benzyl-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-N-hydroxy-acetamide

(2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidinemethylpyrrolidine-2-ethanol

phenyl (2S,3S,4R,5S)-1-benzyl-5-methyl-3,4-isopropylidenedioxypyrrolidine-2-acetate