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

Base Information

Chemical Name:(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone
CAS No.:84362-41-4
Molecular Formula:C₁₉H₃₁NO₅SSi
Molecular Weight:413.61
Hs Code.:

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

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

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

There total 15 articles about (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-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: 68.0%

: 81902-63-8
<3S-<3α(S^*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone

: 98-59-9
p-toluenesulfonyl chloride

: 84362-41-4
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone

Guidance literature:: With pyridine; In tetrahydrofuran; dichloromethane;
DOI:10.1246/bcsj.59.1887

Reference yield:

: 80813-18-9
(3S,4R)-3-<(R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-(methylsulfonyl)-2-azetidinone

: 84362-41-4
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / tetrabutylammonium bromide / benzene; H₂O / 24 h

2: 85 percent / 30percent aq. H₂O₂, 0.5M Na₂CO₃ / H₂O; acetone / 0.5 h / Ambient temperature

3: NaOH / ethanol; H₂O / 1 h / 50 °C

4: ethyl acetate; diethyl ether

5: 78 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 0 °C

6: 68 percent / pyridine / tetrahydrofuran; CH₂Cl₂

With pyridine; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; sodium carbonate; tetrabutylammomium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; benzene;
DOI:10.1246/bcsj.59.1887

Reference yield:

: 84362-43-6
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carbamoyl-2-azetidinone

: 84362-41-4
(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: NaOH / ethanol; H₂O / 1 h / 50 °C

2: ethyl acetate; diethyl ether

3: 78 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 0 °C

4: 68 percent / pyridine / tetrahydrofuran; CH₂Cl₂

With pyridine; sodium hydroxide; sodium tetrahydroborate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1246/bcsj.59.1887