(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

Base Information

Chemical Name:(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one
CAS No.:181957-20-0
Molecular Formula:C₁₈H₂₉NO₂SSi
Molecular Weight:351.585
Hs Code.:

Synonyms:(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

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Chemical Property of (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

There total 1 articles about (3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one 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:

: 1189-71-5
isocyanate de chlorosulfonyle

: tert-Butyl-((E)-(S)-1-ethyl-3-phenylsulfanyl-allyloxy)-dimethyl-silane

: 181957-20-0
(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

: (3S,4R)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

Guidance literature:: With pyridine; thiophenol; Yield given. Multistep reaction. Yields of byproduct given; 1.) i-Pr₂O, RT, 4 h, 2.) i-Pr₂O, -20 deg C, 30 min;
DOI:10.1021/jm9703348

Reference yield: 93.0%

: 84089-26-9
p-nitrobenzyl 1-iodoacetate

: 181957-20-0
(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

: 181957-26-6
p-nitrobenzyl 2-[(3R,4S)-3-(1-(S)-(tert-butyldimethylsilyloxy)propyl)-4-phenylthio-2-azetidinon-1-yl]acetate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 55 ℃; for 4.5h;
DOI:10.1021/jm9703348

Reference yield:

: 181957-20-0
(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-4-phenylsulfanyl-azetidin-2-one

: (5R,6R)-6-((S)-1-Hydroxy-propyl)-7-oxo-3-[(S)-1-(2-oxo-2-phenyl-ethyl)-pyrrolidin-3-ylsulfanyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / K₂CO₃ / dimethylformamide / 4.5 h / 50 - 55 °C

2: 1.) LDA

3: SOCl₂ / CH₂Cl₂ / 0.25 h / -5 °C

4: 1.) morpholine, Et₃N, 2.) Et₃N / 1.) CH₂Cl₂, 10 min, 2.) Ch₂Cl₂, RT, 1 h

5: 72 percent / m-CPBA / CH₂Cl₂ / 1 h / -30 °C

6: i-Pr₂NH / dimethylformamide / 0.33 h

7: tetra-n-butylammonium fluoride, AcOH / tetrahydrofuran / 6 h / 50 °C

8: 20 percent / H₂, phosphate buffer / 10percentPd/C / tetrahydrofuran / Ambient temperature

With morpholine; thionyl chloride; phosphate buffer; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; 10% palladium on active carbon; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm9703348