(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

Base Information

Chemical Name:(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone
CAS No.:112256-78-7
Molecular Formula:C₂₉H₃₃NO₅
Molecular Weight:475.585
Hs Code.:

(3S,4S)-4-<(S)-1-benzyloxyethyl>-1-<bis(p-methoxyphenyl)-methyl>-3-<(R)-1-hydroxyethyl>-2-azetidinone

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

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Technology Process of (3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

There total 18 articles about (3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone 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:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 112256-78-7
(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 69 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / 20 h / Ambient temperature

2: 82 percent / 1.) diisobutylaluminium hydride / 1.) hexane, ether, -78 deg C, 10 min; 2.) MeOH, H₂O, r.t., 1 h

3: MgSO₄ / toluene / 1 h / 0 °C

4: imidazole / CH₂Cl₂ / 69 h / -35 °C

5: 1M potassium triethylborohydride / tetrahydrofuran / 1 h / -78 °C

6: 91 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature

7: 5.1 mg / K₂CO₃ / methanol / 0.17 h / Ambient temperature

With 1H-imidazole; trifluorormethanesulfonic acid; diisobutylaluminium hydride; potassium triethylborohydride; magnesium sulfate; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; toluene;
DOI:10.1016/S0040-4020(01)89105-5

Reference yield:

: 115026-43-2
(3S,4S)-3-acetyl-4-<(S)-1-benzyloxyethyl>-1-(di-p-anisylmethyl)-2-azetidinone

: 115075-46-2
(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(S)-1-hydroxyethyl>-2-azetidinone

: 112256-78-7
(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

Guidance literature:: With potassium triethylborohydride; In tetrahydrofuran; at 0 ℃; Yield given. Yields of byproduct given; further reducting agent;
DOI:10.1016/S0040-4039(00)85317-4

Reference yield:

: 127200-93-5
[Bis-(4-methoxy-phenyl)-methyl]-[(S)-2-(1-ethoxy-ethoxy)-prop-(E)-ylidene]-amine

: 112256-78-7
(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / tetrahydrofuran / 48 h / -30 °C

2: camphorsulfonic acid / methanol / 0.17 h / Ambient temperature

3: 1.) NaH, 2.) 0.5N HCl / 1.) THF, room temp., 1 day, 2.) room temp.

4: potassium triethylborohydride / tetrahydrofuran / 0 °C / further reducting agent

5: 1.) EtOCON=NCOOEt, PPh₃, HCOOH, 2.) K₂CO₃ / 2.) methanol

With 1H-imidazole; hydrogenchloride; formic acid; sodium hydride; potassium triethylborohydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; camphor-10-sulfonic acid; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(00)85317-4