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

Base Information

Chemical Name:benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-hydroxymethyl-1-oxa-3-cephem-4-carboxylate
CAS No.:129441-51-6
Molecular Formula:C₂₃H₃₃NO₆Si
Molecular Weight:447.604
Hs Code.:

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

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

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

There total 9 articles about benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-hydroxymethyl-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: 87.0%

: 129441-50-5
(3R,4R)-1-(benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-(3-hydroxy-2-oxopropane-1-oxy)azetidin-2-one

: 129441-51-6
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-hydroxymethyl-1-oxa-3-cephem-4-carboxylate

Guidance literature:: In toluene; at 100 ℃; for 3.5h;

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

: 129441-51-6
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-hydroxymethyl-1-oxa-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

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

: 129441-51-6
benzyl 7α-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-hydroxymethyl-1-oxa-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 8 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

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