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

Base Information

• Chemical Name: <3α(S^*),4β(E)>-3-(1-hydroxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone
• CAS No.: 77363-79-2
• Molecular Formula: C₂₈H₃₀N₂O₂S
• Molecular Weight: 458.624

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 6 articles about <3α(S^*),4β(E)>-3-(1-hydroxyethyl)-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: 22.0%

<3α(S*),4β(E)>-3-(1-acetoxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-77-0) → <3α(S*),4β(E)>-3-(1-hydroxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-79-2)

Guidance literature:

With sodium hydroxide; In pyridine; at 20 ℃; for 15h;

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

Reference yield:

<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-hydroxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-79-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 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

2: 22 percent / 0.1N NaOH aq. / pyridine / 15 h / 20 °C

With sodium hydroxide; n-butyllithium; benzeneseleninyl chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine;

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

Reference yield:

N-trityl cysteamine (72669-94-4) → <3α(S*),4β(E)>-3-(1-hydroxyethyl)-4-<2-(2-tritylaminoethyl)thiovinyl>-2-azetidinone (77363-79-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 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

3: 22 percent / 0.1N NaOH aq. / pyridine / 15 h / 20 °C

With sodium hydroxide; n-butyllithium; benzeneseleninyl chloride; DBN; sodium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In pyridine;

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

upstream raw materials:

<3α(S^*),4β(E)>-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:

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

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