(3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2

Base Information

• Chemical Name: (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2
• CAS No.: 141599-14-6
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.303
• Mol file: 141599-14-6.mol

Synonyms:

Chemical Property of (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2

There total 8 articles about (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2 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:

N-benzyl-3,4-di-O-benzyl-2-C:1-N-carbonyl-2-deoxy-β-D-arabinopyranosylamine (141599-09-9) → (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2 (141599-14-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

2: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, -5 deg C, 20 min, 2) H₂O, 30 min

3: 2) Merck Kieselgel 60 / 1) ether

With sodium chlorite; sodium periodate; Merck Kieselgel 60; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/S0040-4020(01)90975-5

Reference yield:

benzyl chloride (100-44-7) → (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2 (141599-14-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / K₂CO₃, tetrabutylammonium bromide / benzene / 3 h / Heating

2: 93 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

3: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, -5 deg C, 20 min, 2) H₂O, 30 min

4: 2) Merck Kieselgel 60 / 1) ether

With sodium chlorite; sodium periodate; Merck Kieselgel 60; tetrabutylammomium bromide; hydrogen; dihydrogen peroxide; potassium carbonate; palladium on activated charcoal; In ethyl acetate; benzene;

DOI:10.1016/S0040-4020(01)90975-5

Reference yield:

1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-erythro-pent-1-enitol (116661-76-8) → (3R,4R) 1-benzyl-3-methoxycarbonyl-4-(methoxycarbonyl)methoxy-azetidinone-2 (141599-14-6)

Guidance literature:

Multi-step reaction with 5 steps

2: 66 percent / K₂CO₃, tetrabutylammonium bromide / benzene / 3 h / Heating

3: 93 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h / 760 Torr / Ambient temperature

4: 1) NaIO₄, 2) 35percent hydrogen peroxide, sodium chlorite / 1) t-BuOH, 8percent aq. NH₄H₂PO₄, H₂O, -5 deg C, 20 min, 2) H₂O, 30 min

5: 2) Merck Kieselgel 60 / 1) ether

With sodium chlorite; sodium periodate; Merck Kieselgel 60; tetrabutylammomium bromide; hydrogen; dihydrogen peroxide; potassium carbonate; palladium on activated charcoal; In ethyl acetate; benzene;

DOI:10.1016/S0040-4020(01)90975-5

upstream raw materials:

diazomethane

N-benzyl-2-carboxy-2-deoxy-α-D-arabinopentopyranosylaminolactam

benzyl chloride

1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-erythro-pent-1-enitol