(E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one

Base Information

• Chemical Name: (E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one
• CAS No.: 142039-66-5
• Molecular Formula: C₃₀H₃₈N₂O₄S
• Molecular Weight: 522.709

Synonyms:

Chemical Property of (E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one

There total 1 articles about (E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-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:

acetaldehyde (75-07-0,9002-91-9) + C21H25NO3S (142039-50-7) → (E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one (142039-66-5)

Guidance literature:

Multistep reaction; 1.) -78 deg C;

DOI:10.1021/ja00039a066

Reference yield:

(E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one (142039-66-5) → (3S,4S)-1-benzyl-3-<(S)-1-(t-butyldimethylsiloxy)ethyl>-4-<(E)-styryl>-2-azetidinone (142039-72-3)

Guidance literature:

Multi-step reaction with 9 steps

2: 60 percent / LAH

5: AcOH

6: Swern reagent

7: NaClO₂, NaH₂PO₄

8: CF₃COOH

9: 2-chloro-1-methyl pyridinium iodide

With sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; swern reagent; 2-chloro-1-methyl-pyridinium iodide; acetic acid; trifluoroacetic acid;

DOI:10.1021/ja00039a066

Reference yield:

(E)-(2S,3S)-3-Benzylamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-((S)-1-hydroxy-ethyl)-5-phenyl-pent-4-en-1-one (142039-66-5) → (E)-(2S,3S)-3-Benzylamino-2-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-phenyl-pent-4-enoic acid

Guidance literature:

Multi-step reaction with 8 steps

2: 60 percent / LAH

5: AcOH

6: Swern reagent

7: NaClO₂, NaH₂PO₄

8: CF₃COOH

With sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; swern reagent; acetic acid; trifluoroacetic acid;

DOI:10.1021/ja00039a066

upstream raw materials:

acetaldehyde

C₂₁H₂₅NO₃S

Downstream raw materials:

(E)-(2S,3S)-3-Benzylamino-2-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-phenyl-pent-4-en-1-one

(E)-(2R,3S)-3-Benzylamino-2-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-phenyl-pent-4-en-1-ol

(3S,4S)-1-benzyl-3-<(S)-1-(t-butyldimethylsiloxy)ethyl>-4-<(E)-styryl>-2-azetidinone

Benzyl-[(1S,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-1-((E)-styryl)-2-triethylsilanyloxymethyl-butyl]-amine

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