<3α(S^*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone

Base Information

• Chemical Name: <3α(S^*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone
• CAS No.: 77363-77-0
• Molecular Formula: C₃₀H₃₂N₂O₃S
• Molecular Weight: 500.662

Synonyms:<3α(S^*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone

Chemical Property of <3α(S^*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3α(S^*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone

There total 6 articles about <3α(S^*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-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: 33.0%

<3α(S*),4β(E)>-1-tert-butoxycarbonylmethyl-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-76-9,77448-32-9) → <3α(S*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-77-0)

Guidance literature:

With Phenylselenyl chloride; LiN(SiMe₃); In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)92204-4

Reference yield:

[(2R,3R)-3-((S)-1-Acetoxy-ethyl)-2-(2-chloro-1-phenylsulfanyl-ethyl)-4-oxo-azetidin-1-yl]-acetic acid tert-butyl ester (76671-17-5,77448-30-7,77448-36-3) → <3α(S*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-77-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / m-chloroperbenzoic acid / CHCl₃ / 0.5 h / 0 °C

2: 97 percent / DBU / tetrahydrofuran / 1 h / 25 °C

3: 1.) 1,5-diazabicyclo(4,3,0)non-5-ene, 2.) Na₂CO₃ / 1.) benzene, at 0 degC, 5 min, 2.) toluene, 1 h, reflux

4: 1.) 1,1,1,3,3,3-hexamethyldisilazane, n-butyllithium, 2.) phenylseleninyl chloride / 1.) THF, n-hexane, 0 degC, 5 min, then -78 degC, 10 min, 2.) THF, -78 degC

With n-butyllithium; benzeneseleninyl chloride; DBN; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; chloroform;

DOI:10.1016/0040-4020(82)85029-1

Reference yield:

[(2R,3R)-3-((S)-1-Acetoxy-ethyl)-2-(1-benzenesulfinyl-2-chloro-ethyl)-4-oxo-azetidin-1-yl]-acetic acid tert-butyl ester (86531-49-9,86561-98-0,86562-04-1,86562-05-2) → <3α(S*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-77-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / DBU / tetrahydrofuran / 1 h / 25 °C

2: 1.) 1,5-diazabicyclo(4,3,0)non-5-ene, 2.) Na₂CO₃ / 1.) benzene, at 0 degC, 5 min, 2.) toluene, 1 h, reflux

3: 1.) 1,1,1,3,3,3-hexamethyldisilazane, n-butyllithium, 2.) phenylseleninyl chloride / 1.) THF, n-hexane, 0 degC, 5 min, then -78 degC, 10 min, 2.) THF, -78 degC

With n-butyllithium; benzeneseleninyl chloride; DBN; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran;

DOI:10.1016/0040-4020(82)85029-1

upstream raw materials:

<3α(S^*),4β(E)>-1-tert-butoxycarbonylmethyl-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone

N-trityl cysteamine

[(2R,3R)-3-((S)-1-Acetoxy-ethyl)-2-(1-benzenesulfinyl-vinyl)-4-oxo-azetidin-1-yl]-acetic acid tert-butyl ester

[(2R,3R)-3-((S)-1-Acetoxy-ethyl)-2-(2-chloro-1-phenylsulfanyl-ethyl)-4-oxo-azetidin-1-yl]-acetic acid tert-butyl ester

Downstream raw materials:

(E)-(2R,3R)-2-((S)-1-Acetoxy-ethyl)-3-amino-5-[2-(trityl-amino)-ethylsulfanyl]-pent-4-enoic acid methyl ester

<3α(S^*),4β(E)>-3-(1-hydroxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone

<3α(S^*),4β(E)>-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-<2-(2-p-nitrobenzyloxycarbonylaminoethyl)thiovinyl>-2-azetidinone

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