(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

Base Information

Chemical Name:(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone
CAS No.:118735-54-9
Molecular Formula:C₂₀H₃₃NO₅SSi
Molecular Weight:427.637
Hs Code.:

Synonyms:(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

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Chemical Property of (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

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Technology Process of (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

There total 11 articles about (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-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: 85.0%

: 115075-47-3
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<(S)-1-hydroxyethyl>-2-azetidinone

: 98-59-9
p-toluenesulfonyl chloride

: 118735-54-9
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

Guidance literature:: In pyridine; at 0 ℃; for 12h;
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

: 118735-54-9
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: 5.1 mg / K₂CO₃ / methanol / 0.17 h / Ambient temperature

4: 93 percent / CAN / acetonitrile; H₂O / 3 h / -10 °C

5: 97 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

6: hydrogen / 10percent Pd/C / ethyl acetate

7: 85 percent / pyridine / 12 h / 0 °C

With 1H-imidazole; ammonium cerium(IV) nitrate; hydrogen; potassium triethylborohydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)89105-5

Reference yield:

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

: 118735-54-9
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>4-<(S)-1-(p-toluenesulfonyloxy)ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: hydrogen / 10percent Pd/C / ethyl acetate

3: 85 percent / pyridine / 12 h / 0 °C

With 1H-imidazole; hydrogen; palladium on activated charcoal; In pyridine; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89105-5