benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

Base Information

Chemical Name:benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate
CAS No.:129441-57-2
Molecular Formula:C₂₃H₃₀N₂O₅Si
Molecular Weight:442.587
Hs Code.:

Synonyms:benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

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Chemical Property of benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

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Technology Process of benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

There total 12 articles about benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate 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: 100.0%

: 129441-56-1
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-hydroxyiminomethyl-1-oxa-3-cephem-4-carboxylate

: 129441-57-2
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

Guidance literature:: With pyridine; thionyl chloride; In dichloromethane; for 2h; Ambient temperature;

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

: 129441-57-2
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 86 percent / zinc acetate / benzene / 8.5 h / Heating

2: 49 percent / 1.) oxalyl chloride, DMSO, 2.) Et₃N / CH₂Cl₂ / -50 °C / 1.) 15 min, 2.) 1 h

3: Et₃N / tetrahydrofuran / 3 h / Ambient temperature

4: 2,6-lutidine, thionyl chloride / CH₂Cl₂ / 0.75 h / -40 °C

5: CH₂Cl₂ / Ambient temperature

6: 60 percent / 5.18 M NaOMe / methanol / 2.5 h / -40 °C

7: 87 percent / toluene / 3.5 h / 100 °C

8: 99 percent / 1.) oxalyl chloride, DMSO, 2.) Et₃N / CH₂Cl₂ / -40 °C / 1.) 20 min, 2.) 1 h

9: 100 percent / hydroxylamine hydrochloride / tetrahydrofuran; H₂O / 2 h / Ambient temperature

10: 100 percent / pyridine, thionyl chloride / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; thionyl chloride; oxalyl dichloride; hydroxylamine hydrochloride; zinc diacetate; sodium methylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene;

Reference yield:

: 123657-02-3
(3R,4R)-4-allyloxy-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>azetidin-2-one

: 129441-57-2
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-cyano-1-oxa-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 91 percent / 70percent m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / Ambient temperature

2: 77 percent / Ti(iOPr)4 / 6 h / Ambient temperature

3: 49 percent / 1.) oxalyl chloride, DMSO, 2.) Et₃N / CH₂Cl₂ / -50 °C / 1.) 15 min, 2.) 1 h

4: Et₃N / tetrahydrofuran / 3 h / Ambient temperature

5: 2,6-lutidine, thionyl chloride / CH₂Cl₂ / 0.75 h / -40 °C

6: CH₂Cl₂ / Ambient temperature

7: 60 percent / 5.18 M NaOMe / methanol / 2.5 h / -40 °C

8: 87 percent / toluene / 3.5 h / 100 °C

9: 99 percent / 1.) oxalyl chloride, DMSO, 2.) Et₃N / CH₂Cl₂ / -40 °C / 1.) 20 min, 2.) 1 h

10: 100 percent / hydroxylamine hydrochloride / tetrahydrofuran; H₂O / 2 h / Ambient temperature

11: 100 percent / pyridine, thionyl chloride / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; thionyl chloride; oxalyl dichloride; hydroxylamine hydrochloride; sodium methylate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; toluene;