(2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

Base Information

Chemical Name:(2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid
CAS No.:1558079-15-4
Molecular Formula:C₂₂H₃₂N₂O₆Si
Molecular Weight:448.591
Hs Code.:

Synonyms:(2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

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Chemical Property of (2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

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Technology Process of (2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

There total 7 articles about (2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid 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: 78.0%

: 1558079-14-3
(2S,6S,7S)-4-benzyloxy-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-vinyl-1,4-diazabicyclo[4.2.0]octane-5,8-dione

: 1558079-15-4
(2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

Guidance literature:: With potassium permanganate; sodium periodate; sodium hydrogencarbonate; In water; acetone; at 20 ℃; for 17h; Inert atmosphere;
DOI:10.1021/jo402544p

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 1558079-15-4
(2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: sodium iodide; indium / N,N-dimethyl-formamide / 24 h / 20 °C

2: RuHCl(CO)(PPh₃)3 / tetrahydrofuran / 4 h / 76 °C / Inert atmosphere

3: potassium permanganate; sodium periodate; sodium hydrogencarbonate / acetone; water / 19 h / 20 °C

4: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / acetonitrile / 24 h / 20 °C / Inert atmosphere

5: palladium diacetate; p-benzoquinone; acetic acid / acetonitrile / 48 h / 45 °C

6: potassium permanganate; sodium periodate; sodium hydrogencarbonate / acetone; water / 17 h / 20 °C / Inert atmosphere

With dmap; indium; potassium permanganate; sodium periodate; RuHCl(CO)(PPh₃)3; palladium diacetate; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; p-benzoquinone; sodium iodide; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo402544p

Reference yield:

: 80433-47-2
(3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(prop-2-enyl)-2-azetidinone

: 1558079-15-4
(2R,6S,7S)-4-(benzyloxy)-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5,8-dioxo-1,4-diazabicyclo[4.2.0]octane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: RuHCl(CO)(PPh₃)3 / tetrahydrofuran / 4 h / 76 °C / Inert atmosphere

2: potassium permanganate; sodium periodate; sodium hydrogencarbonate / acetone; water / 19 h / 20 °C

3: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / acetonitrile / 24 h / 20 °C / Inert atmosphere

4: palladium diacetate; p-benzoquinone; acetic acid / acetonitrile / 48 h / 45 °C

5: potassium permanganate; sodium periodate; sodium hydrogencarbonate / acetone; water / 17 h / 20 °C / Inert atmosphere

With dmap; potassium permanganate; sodium periodate; RuHCl(CO)(PPh₃)3; palladium diacetate; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; p-benzoquinone; In tetrahydrofuran; water; acetone; acetonitrile;
DOI:10.1021/jo402544p