(+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone

Base Information

• Chemical Name: (+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone
• CAS No.: 614733-16-3
• Molecular Formula: C₁₈H₁₈INO₃
• Molecular Weight: 423.25
• Mol file: 614733-16-3.mol

Synonyms:(+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone

Chemical Property of (+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone

There total 1 articles about (+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone 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:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone (148968-08-5) → (+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone (614733-16-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

2: 100 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 20 °C

3: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

With dmap; sodium tetrahydroborate; sodium hydrogencarbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)01063-9

Reference yield: 92.0%

(+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone (614733-16-3) → (+)-(3R,4S)-1-(p-anisyl)-4-methyl-3-(benzyloxy)-2-azetidinone (614733-17-4)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In ethanol; for 2h; under 2585.74 Torr;

DOI:10.1016/S0040-4020(03)01063-9

Reference yield:

(+)-(3R,4R)-1-(p-anisyl)-4-iodomethyl-3-(benzyloxy)-2-azetidinone (614733-16-3) → (+)-(5S,6S)-1-benzyl-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone (614733-24-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / NaHCO₃; H₂ / Pd/C / ethanol / 2 h / 2585.74 Torr

2: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

3: 93 percent / 4-(dimethylamino)pyridine / acetonitrile / 4 h / 20 °C

4: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

5: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

6: methanol / 12 h / 20 °C

7: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8: 4-(dimethylamino)pyridine / toluene / 1 h / Heating

9: 87 percent / NaH; Bu₄NI / tetrahydrofuran / 2.17 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(03)01063-9

upstream raw materials:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

Downstream raw materials:

(+)-(3R,4S)-1-(p-anisyl)-4-methyl-3-(benzyloxy)-2-azetidinone

(-)-(5S,6S)-1-benzyl-5-(benzyloxy)6-methyl-hexahydro-2-pyridinone

(+)-(3R,4S)-4-methyl-3-(benzyloxy)-2-azetidinone

(+)-(5S,6S)-5-(benzyloxy)-6-methyl-1,2,5,6-tetrahydro-2-pyridinone