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

Base Information

Chemical Name:2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid benzyl ester
CAS No.:79975-82-9
Molecular Formula:C₁₆H₁₇N₃O₅
Molecular Weight:331.328
Hs Code.:

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

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

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

There total 13 articles about 2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-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:

: 62263-73-4
(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

: 79975-82-9
2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 7 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

7: conc. HCl / methanol; H₂O / 24 h / Ambient temperature

With hydrogenchloride; potassium permanganate; silver tetrafluoroborate; TEA; potassium tert-butylate; chlorine; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00412a048

Reference yield:

: 79975-80-7
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-chloro-azetidin-2-one

: 79975-82-9
2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / AgBF₄ / acetonitrile / 2 h / Ambient temperature

2: conc. HCl / methanol; H₂O / 24 h / Ambient temperature

With hydrogenchloride; silver tetrafluoroborate; In methanol; water; acetonitrile;
DOI:10.1021/ja00412a048

Reference yield:

: 79975-77-2
benzyl 6-acetylpenicillanate

: 79975-82-9
2-Diazo-4-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: magnesium trifluoroacetate, diisopropylamine-borane / diethyl ether / 1.25 h / 0 °C

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

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

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

6: Cl₂ / CCl₄

7: 70 percent / AgBF₄ / acetonitrile / 2 h / Ambient temperature

8: conc. HCl / methanol; H₂O / 24 h / Ambient temperature

With hydrogenchloride; potassium permanganate; silver tetrafluoroborate; diisopropylamine borane; TEA; potassium tert-butylate; magnesium(II) 2,2,2-trifluoroacetate; chlorine; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00412a048