4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester

Base Information

• Chemical Name: 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester
• CAS No.: 79975-87-4
• Molecular Formula: C₂₈H₄₅N₃O₅Si₂
• Molecular Weight: 559.853
• Mol file: 79975-87-4.mol

Synonyms:4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester

Chemical Property of 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester

There total 8 articles about 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester 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: 70.0%

Benzyl α-diazoacetoacetate trimethylsilyl enol ether (79975-81-8) + (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-azetidin-2-one (79975-80-7) → 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester (79975-87-4)

Guidance literature:

With silver tetrafluoroborate; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/ja00412a048

Reference yield:

benzyl-α-diazo-acetoacetate (52267-50-2) → 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester (79975-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hexamethyldisilazane, tetramethylethylenediamine / tetrahydrofuran / -78 deg C -> 0 deg C

2: 70 percent / AgBF₄ / acetonitrile / 2 h / Ambient temperature

With silver tetrafluoroborate; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ja00412a048

Reference yield:

(5R)-6c-((R)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester (62263-73-4) → 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid benzyl ester (79975-87-4)

Guidance literature:

Multi-step reaction with 6 steps

2: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature

3: KMnO₄ / pyridine; H₂O / 4 h / 25 °C

4: TEA / dimethylformamide / 4 h / 25 °C

5: Cl₂ / CCl₄

6: 70 percent / AgBF₄ / acetonitrile / 2 h / Ambient temperature

With potassium permanganate; silver tetrafluoroborate; TEA; potassium tert-butylate; chlorine; In tetrahydrofuran; pyridine; tetrachloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00412a048

upstream raw materials:

Benzyl α-diazoacetoacetate trimethylsilyl enol ether

(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-azetidin-2-one

benzyl-α-diazo-acetoacetate

(5R)-6c-((R)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester

Downstream raw materials:

2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid benzyl ester

(2R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester