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

Base Information

• Chemical Name: (+)-(3R,4S)-1-(p-anisyl)-4-(methanesulfonyloxymethyl)-3-benzyloxy-2-azetidinone
• CAS No.: 614733-15-2
• Molecular Formula: C₁₉H₂₁NO₆S
• Molecular Weight: 391.445
• Mol file: 614733-15-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (+)-(3R,4S)-1-(p-anisyl)-4-(methanesulfonyloxymethyl)-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: 100.0%

methanesulfonyl chloride (124-63-0) + (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone (160237-99-0) → (+)-(3R,4S)-1-(p-anisyl)-4-(methanesulfonyloxymethyl)-3-benzyloxy-2-azetidinone (614733-15-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 6h;

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

Reference yield:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone (148968-08-5) → (+)-(3R,4S)-1-(p-anisyl)-4-(methanesulfonyloxymethyl)-3-benzyloxy-2-azetidinone (614733-15-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; dichloromethane; water;

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

Reference yield:

(+)-(3R,4S)-1-(p-anisyl)-4-(methanesulfonyloxymethyl)-3-benzyloxy-2-azetidinone (614733-15-2) → (2R,3S)-3-[(tert-butyloxycarbonyl)amino]-2-(benzyloxy)butanal (614733-21-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / NaI; NaHCO₃ / dimethylformamide / 6 h / 60 - 70 °C

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

3: 76 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

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

5: 87 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

6: 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

With dmap; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; hydrogen; sodium hydrogencarbonate; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

methanesulfonyl chloride

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone

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

Downstream raw materials:

(-)-(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

(+)-(3R,4S)-1-(tert-butyloxycarbonyl)-4-methyl-3-(benzyloxy)-2-azetidinone