(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
• Mol file: 84362-41-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

<3S-<3α(S*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone (81902-63-8) + p-toluenesulfonyl chloride (98-59-9) → (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone (84362-41-4)

Guidance literature:

With pyridine; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.59.1887

Reference yield:

(3S,4R)-3-<(R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-(methylsulfonyl)-2-azetidinone (80813-18-9) → (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone (84362-41-4)

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:

(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-carbamoyl-2-azetidinone (84362-43-6) → (3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-(p-tolylsulfonyloxymethyl)-2-azetidinone (84362-41-4)

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

upstream raw materials:

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

p-toluenesulfonyl chloride

benzyl (2S,5R,6R)-6-<(R)-1-hydroxyethyl>penicillanate

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

Downstream raw materials:

p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-chloroacetate

p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-hydroxyacetate

p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-hydroxyethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

p-nitrobenzyl (2S,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate