(1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 1334521-80-0
• Molecular Formula: C₂₃H₂₄N₂O₆S
• Molecular Weight: 456.519
• Mol file: 1334521-80-0.mol

Synonyms:(1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

There total 6 articles about (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate 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: 48.0%

(4R,5S)-benzyl 4-((2-(benzyloxy)-2-oxoethoxy)carbamoyl)-5-hydroxy-2,2-dimethylthiazolidine-3-carboxylate (1334521-66-2) → (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate (1334521-80-0)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at -20 ℃;

DOI:10.1016/j.tetlet.2011.07.085

Reference yield:

C19H25NO6S → (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate (1334521-80-0)

Guidance literature:

Multi-step reaction with 4 steps

1: -20 °C

2: oxygen / tetrahydrofuran / -10 - 0 °C / UV-irradiation

3: dimethylsulfide / tetrahydrofuran / 20 °C

4: methanesulfonyl chloride; triethylamine / dichloromethane / -20 °C

With dimethylsulfide; oxygen; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; 2: Pummerer type rearrangement;

DOI:10.1016/j.tetlet.2011.07.085

Reference yield:

C23H26N2O8S → (1R,5R)-benzyl 6-(2-benzyloxy-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate (1334521-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfide / tetrahydrofuran / 20 °C

2: methanesulfonyl chloride; triethylamine / dichloromethane / -20 °C

With dimethylsulfide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2011.07.085

upstream raw materials:

(R)-benzyl 4-((2-(benzyloxy)-2-oxoethoxy)carbamoyl)-2,2-dimethylthiazolidine-3-carboxylate

(4R,5S)-benzyl 4-((2-(benzyloxy)-2-oxoethoxy)carbamoyl)-5-hydroxy-2,2-dimethylthiazolidine-3-carboxylate

benzyl 2-(aminooxy)acetate