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

Base Information

Chemical Name:(2S,6S,7S)-4-benzyloxy-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-vinyl-1,4-diazabicyclo[4.2.0]octane-5,8-dione
CAS No.:1558079-14-3
Molecular Formula:C₂₃H₃₄N₂O₄Si
Molecular Weight:430.619
Hs Code.:

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

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

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

There total 5 articles about (2S,6S,7S)-4-benzyloxy-7-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-vinyl-1,4-diazabicyclo[4.2.0]octane-5,8-dione 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: 54.0%

: (2S,3S)-N-(benzyloxy)-N-(but-2-en-1-yl)-3-((R)-1-((tertbutyldimethylsilyl)oxy)ethyl)-4-oxoazetidine-2-carboxamide

: 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

Guidance literature:: With palladium diacetate; acetic acid; p-benzoquinone; In acetonitrile; at 45 ℃; for 48h;
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

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

Guidance literature:: Multi-step reaction with 5 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

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

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

Guidance literature:: Multi-step reaction with 4 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

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