(3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole

Base Information

• Chemical Name: (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole
• CAS No.: 1369963-66-5
• Molecular Formula: C₁₅H₁₉NO₅S
• Molecular Weight: 325.386
• Mol file: 1369963-66-5.mol

Synonyms:(3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole

Chemical Property of (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole

There total 1 articles about (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-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:

PVS (5535-48-8) + 3,4-isopropylidenedioxy-Δ1-pyrroline-1-oxide (213598-45-9) → (3R,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-65-4) + (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-66-5) + (2S,3aS,4S,5R)-2-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-68-7) + (2R,3aS,4S,5R)-2-pchenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-67-6)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 16h; optical yield given as %de; regioselective reaction;

DOI:10.1016/j.tetasy.2012.01.006

Reference yield: 100.0%

(3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-66-5) → (3R,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-65-4)

Guidance literature:

In toluene; at 110 ℃; for 72h;

DOI:10.1016/j.tetasy.2012.01.006

Reference yield: 74.0%

(3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole (1369963-66-5) + methylmagnesium bromide (75-16-1) → (1′R,2R,3S,4R)-2-[(1′-phenylsulfonyl)propyl]-1-hydroxy-3,4-isopropylidenedioxypyrrolidine (1446141-81-6)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jo400873c

upstream raw materials:

PVS

3,4-isopropylidenedioxy-Δ¹-pyrroline-1-oxide

Downstream raw materials:

(3R,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole

(1′R,2R,3S,4R)-2-[(1′-phenylsulfonyl)hexyl]-1-hydroxy-3,4-isopropylidenedioxypyrrolidine

(1′R,2R,3S,4R)-2-[(1′-phenylsulfonyl)(3′-methyl)pentyl]-1-hydroxy-3,4-isopropylidenedioxypyrrolidine

(1′R,2R,3S,4R)-2-[(1′-phenylsulfonyl)(4′-methyl)pent-4′-enyl]-1-hydroxy-3,4-isopropylidenedioxypyrrolidine