N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane

Base Information

• Chemical Name: N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane
• CAS No.: 291523-46-1
• Molecular Formula: C₂₁H₂₄BrNO₃S
• Molecular Weight: 450.396

Synonyms:N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane

Chemical Property of N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane

Chemical Property:

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Technology Process of N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane

There total 1 articles about N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane 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: 84.0%

(E)-3-phenylpropenal (14371-10-9) + N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.01,5>decane (167259-92-9) → N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.01,5]decane (291523-46-1)

Guidance literature:

N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine;

(E)-3-phenylpropenal; Further stages.;

DOI:10.1021/jo000124u

Reference yield: 89.0%

N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.01,5]decane (291523-46-1) → (R)-3-hydroxy-5-phenyl-(E)-4-pentenoic acid

Guidance literature:

N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane; With water; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

With aluminium amalgam; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1021/jo000124u

Reference yield:

N-[(2R,3S)-2-bromo-3-hydroxy-4-methyl-(E)-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.01,5]decane (291523-46-1) + benzyl alcohol (100-51-6,185532-71-2) → (E)-(2R,3S)-2-Bromo-3-hydroxy-5-phenyl-pent-4-enoic acid benzyl ester

Guidance literature:

With dmap; In acetonitrile; at 0 ℃; for 4h;

DOI:10.1016/S0957-4166(00)00109-9

upstream raw materials:

(E)-3-phenylpropenal

N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane

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