(1R,5R)-tert-butyl 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)-tert-butyl 6-(2-(benzyloxy)-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate
CAS No.:1334521-78-6
Molecular Formula:C₂₀H₂₆N₂O₆S
Molecular Weight:422.502
Hs Code.:

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

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

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Technology Process of (1R,5R)-tert-butyl 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)-tert-butyl 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: 45.0%

: 1334521-64-0
(4R,5S)-tert-butyl 4-(((benzyloxycarbonyl)methoxy)carbamoyl)-5-hydroxy-2,2-dimethylthiazolidine-3-carboxylate

: 1334521-78-6
(1R,5R)-tert-butyl 6-(2-(benzyloxy)-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at -20 ℃;
DOI:10.1016/j.tetlet.2011.07.085

Reference yield:

: 5317-15-7
(4R)-3-(tert-butoxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid

: 1334521-78-6
(1R,5R)-tert-butyl 6-(2-(benzyloxy)-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 4-methyl-morpholine / 0.5 h / 0 °C

2: -20 °C

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

4: dimethylsulfide / tetrahydrofuran / 20 °C

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

With 4-methyl-morpholine; dimethylsulfide; oxygen; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; 3: Pummerer type rearrangement;
DOI:10.1016/j.tetlet.2011.07.085

Reference yield:

: C₁₆H₂₇NO₆S

: 1334521-78-6
(1R,5R)-tert-butyl 6-(2-(benzyloxy)-2-oxoethoxy)-3,3-dimethyl-7-oxo-4-thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

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