2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole

Base Information

• Chemical Name: 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole
• CAS No.: 634610-96-1
• Molecular Formula: C₂₈H₂₆N₂O₇S
• Molecular Weight: 534.59
• Mol file: 634610-96-1.mol

Synonyms:2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole

Chemical Property of 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole

There total 9 articles about 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole 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: 92.0%

4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol (49787-02-2) + 2-O-[4'-(2''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-mannitole (634610-94-9) → 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole (634610-96-1)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1055/s-2003-41426

Reference yield:

(3R,3aR,6R,6aR)-6-benzyloxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (183624-93-3) → 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole (634610-96-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 1 h / 60 °C

1.2: 92 percent / dimethylformamide / 60 °C

2.1: H₂ / Pd/C / methanol; tetrahydrofuran / 0.5 h / 750.06 Torr

3.1: 4.46 g / KNO₂; KI; aq. HBr / dimethylsulfoxide / 0.5 h / 50 °C

4.1: 70 percent / PPh₃; Ba(OH)2*8H₂O / Pd₂(dba)3 / 1,2-dimethoxy-ethane / 4 h / Heating

5.1: 86 percent / aq. magnesium monoperoxyphthalate / ethanol; CH₂Cl₂ / 36 h / 50 °C

6.1: 92 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 40 °C

With barium dihydroxide; potassium nitrite; di-isopropyl azodicarboxylate; hydrogen bromide; hydrogen; sodium hydride; magnesium monoperoxyphthalate hexahydrate; triphenylphosphine; potassium iodide; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Suzuki coupling / 6.1: Mitsunobu reaction;

Reference yield:

1,4:3,6-dianhydro-D-mannitol (641-74-7) → 2-O-[4'-(5''-methyl[1,2,4]oxadiazol-3''-yl)phenyl]-5-O-[4'''-(2''''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-sorbitole (634610-96-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 80 °C

1.2: 48 percent / TBAI / dimethylformamide / 18 h / 20 °C

2.1: NaH / dimethylformamide / 1 h / 60 °C

2.2: 92 percent / dimethylformamide / 60 °C

3.1: H₂ / Pd/C / methanol; tetrahydrofuran / 0.5 h / 750.06 Torr

4.1: 4.46 g / KNO₂; KI; aq. HBr / dimethylsulfoxide / 0.5 h / 50 °C

5.1: 70 percent / PPh₃; Ba(OH)2*8H₂O / Pd₂(dba)3 / 1,2-dimethoxy-ethane / 4 h / Heating

6.1: 86 percent / aq. magnesium monoperoxyphthalate / ethanol; CH₂Cl₂ / 36 h / 50 °C

7.1: 92 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 40 °C

With barium dihydroxide; potassium nitrite; di-isopropyl azodicarboxylate; hydrogen bromide; hydrogen; sodium hydride; magnesium monoperoxyphthalate hexahydrate; triphenylphosphine; potassium iodide; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 5.1: Suzuki coupling / 7.1: Mitsunobu reaction;

upstream raw materials:

4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol

2-O-[4'-(2''-methylsulfonylphenyl)phenyl]-1,4:3,6-dianhydro-D-mannitole

4-Fluoronitrobenzene

(3R,3aR,6R,6aR)-6-benzyloxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol