(R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate

Base Information

• Chemical Name: (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate
• CAS No.: 1339193-36-0
• Molecular Formula: C₂₄H₂₅NO₈S
• Molecular Weight: 487.53
• Mol file: 1339193-36-0.mol

Synonyms:

Chemical Property of (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate

There total 4 articles about (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate 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:

[(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester (868082-97-7) → (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate (1339193-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium diisopropyl amide / tetrahydrofuran / 4 h / -78 - 20 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / acetonitrile / 0 - 20 °C / Inert atmosphere

3: tin(IV) chloride / dichloromethane; benzene / 2.5 h / Reflux

With boron trifluoride diethyl etherate; tin(IV) chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;

DOI:10.1002/cmdc.201100282

Reference yield:

(E)-benzyl 2-{(S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-1-(methylthio)-4-oxoazetidin-2-ylidene}acetate (1339193-17-7) → (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate (1339193-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / acetonitrile / 0 - 20 °C / Inert atmosphere

2: tin(IV) chloride / dichloromethane; benzene / 2.5 h / Reflux

With boron trifluoride diethyl etherate; tin(IV) chloride; In dichloromethane; acetonitrile; benzene;

DOI:10.1002/cmdc.201100282

Reference yield:

3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4) → (R)-1-{(S,E)-2-[2-(benzyloxy)-2-oxoethylidene]-1-(methylthio)-4-oxoazetidin-3-yl}ethyl 4-hydroxy-3,5-dimethoxybenzoate (1339193-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl dichloride / dichloromethane / 2 h / Inert atmosphere; Reflux

2: tin(IV) chloride / dichloromethane; benzene / 2.5 h / Reflux

With oxalyl dichloride; tin(IV) chloride; In dichloromethane; benzene;

DOI:10.1002/cmdc.201100282

upstream raw materials:

[(S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-(2E)-ylidene]-acetic acid benzyl ester

(E)-benzyl 2-((S)-3-((R)-1-hydroxyethyl)-1-(methylthio)-4-oxoazetidin-2-ylidene)acetate

3,5-dimethoxy-4-hydroxybenzoic acid chloride

(E)-benzyl 2-{(S)-3-[(1R)-1-(tert-butyldimethylsilanyloxy)ethyl]-1-(methylthio)-4-oxoazetidin-2-ylidene}acetate