tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate

Base Information

• Chemical Name: tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate
• CAS No.: 1380110-40-6
• Molecular Formula: C₃₀H₃₅N₅O₇
• Molecular Weight: 577.637
• Mol file: 1380110-40-6.mol

Synonyms:tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate

Chemical Property of tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate

There total 18 articles about tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate 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: 61.0%

tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)-carbamate (1380110-39-3) → tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate (1380110-40-6)

Guidance literature:

With dipotassium hydrogenphosphate; dipotassium peroxodisulfate; In water; acetonitrile; at 70 - 72 ℃; for 2.5h; pH=6.3 - 7; Inert atmosphere;

DOI:10.1021/acs.oprd.9b00374

Reference yield: 60.0%

C39H46N6O9 → tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate (1380110-40-6)

Guidance literature:

With potassium phosphate; dipotassium peroxodisulfate; In water; acetonitrile; at 75 ℃; for 1.5h;

DOI:10.1021/jm400560z

Reference yield:

CH4O3S*C20H20N2O3 (1380112-29-7) → tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)carbamate (1380110-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tripotassium phosphate "n" hydrate / dichloromethane; water / 1 h / 22 °C

1.2: 4 h / 22 °C / Inert atmosphere

1.3: 15 h / 22 - 40 °C

2.1: dipotassium hydrogenphosphate; dipotassium peroxodisulfate / water; acetonitrile / 1.5 h / 75 °C / pH 6 - 6.5

With dipotassium hydrogenphosphate; dipotassium peroxodisulfate; tripotassium phosphate "n" hydrate; In dichloromethane; water; acetonitrile;

upstream raw materials:

benzyl bromide

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

tert-butyl ((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)-carbamate

C₂₀H₁₉NO₄

Downstream raw materials:

2-((((Z)-2-(((2R,3S)-2-((3-((1,5-bis-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)-methyl)-4-oxoazetidin-3-yl)amino)-1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoethylidene)-amino)oxy)-2-methylpropanoic acid tert-butyl ester

(2R,3S)-2-((3-((1,5-bis(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl)ureido)methyl)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid

C₄₈H₅₄N₈O₁₁S

1-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl)-2-({(2R,3S)-2-[({[(1,5-dihydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl]carbamoyl}amino)methyl]-4-oxo-1-sulfoazetidin-3-yl}amino)-2-oxoethylidene]amino}oxy)cyclohexane carboxylic acid