tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

Base Information

Chemical Name:tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate
CAS No.:130163-99-4
Molecular Formula:C₁₆H₃₆N*C₁₉H₂₃N₂O₉S
Molecular Weight:697.934
Hs Code.:

tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

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Chemical Property of tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

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Technology Process of tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

There total 6 articles about tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate 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:

: 112256-71-0
(3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-hydroxyethyl>-2-azetidinone

: 130163-99-4
tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: 100 percent / 1N HCl, hydrogen / 5percent Pd-C / tetrahydrofuran / 5.5 h / Ambient temperature

3: 97 percent / pyridine / 17 h / Ambient temperature

4: 91 percent / methanol

5: 1) methanolic 1N HCl, 2) 4-N,N-dimethylaminopyridine / 1) MeOH, r.t., 0.5 h, 2) CH₂Cl₂, r.t., 13 h

6: 1) sulfur trioxide-pyridine complex, 2) 0.5M KH₂PO₄ / 1) DMF, 50 deg C, 6 h

With pyridine; hydrogenchloride; dmap; potassium dihydrogenphosphate; hydrogen; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1248/cpb.38.917

Reference yield:

: 130163-56-3
(3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-tetrahydropyran-2-yloxyethyl>-2-azetidinone

: 130163-99-4
tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / 1N HCl, hydrogen / 5percent Pd-C / tetrahydrofuran / 5.5 h / Ambient temperature

2: 97 percent / pyridine / 17 h / Ambient temperature

3: 91 percent / methanol

4: 1) methanolic 1N HCl, 2) 4-N,N-dimethylaminopyridine / 1) MeOH, r.t., 0.5 h, 2) CH₂Cl₂, r.t., 13 h

5: 1) sulfur trioxide-pyridine complex, 2) 0.5M KH₂PO₄ / 1) DMF, 50 deg C, 6 h

With pyridine; hydrogenchloride; dmap; potassium dihydrogenphosphate; hydrogen; sulfur trioxide pyridine complex; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1248/cpb.38.917

Reference yield:

: 130163-57-4
(3S,4S)-3-<(R)-1-tetrahydropyran-2-yloxyethyl>-4-<(S)-1-hydroxyethyl>-2-azetidinone

: 130163-99-4
tetrabutylammonium (3S,4S)-3-<(R)-1-(benzyloxycarbonyloxy)ethyl>-4-<(S)-1-(N-cyclopropylcarbamoyloxy)ethyl>-2-azetidinone-1-sulfonate

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / pyridine / 17 h / Ambient temperature

2: 91 percent / methanol

3: 1) methanolic 1N HCl, 2) 4-N,N-dimethylaminopyridine / 1) MeOH, r.t., 0.5 h, 2) CH₂Cl₂, r.t., 13 h

4: 1) sulfur trioxide-pyridine complex, 2) 0.5M KH₂PO₄ / 1) DMF, 50 deg C, 6 h

With pyridine; hydrogenchloride; dmap; potassium dihydrogenphosphate; sulfur trioxide pyridine complex; In methanol;
DOI:10.1248/cpb.38.917