N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane

Base Information

• Chemical Name: N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane
• CAS No.: 226067-50-1
• Molecular Formula: C₁₉H₂₂BrNO₃S
• Molecular Weight: 424.359

Synonyms:N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane

Chemical Property of N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane

Chemical Property:

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Technology Process of N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^1,5]decane

There total 1 articles about N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o^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: 94.0%

benzaldehyde (100-52-7) + 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-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o1,5]decane (226067-50-1)

Guidance literature:

N-Acetyl-(1S,5R,7R)-10,10-Dimethyl-3-thioxo-2-aza-4-oxatricyclo<5.2.1.0^1,5>decane; With bromine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃;

benzaldehyde; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1021/jo990444h

Reference yield: 98.0%

N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o1,5]decane (226067-50-1) → (2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoic acid (226067-54-5)

Guidance literature:

With triethylamine; In dichloromethane; water; at 0 ℃;

DOI:10.1016/S0040-4039(99)00576-6

Reference yield: 96.0%

N-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropionyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.o1,5]decane (226067-50-1) + benzyl alcohol (100-51-6,185532-71-2) → phenylmethyl (2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoate

Guidance literature:

With dmap; In dichloromethane; at 0 ℃;

DOI:10.1021/jo990444h

upstream raw materials:

benzaldehyde

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

Downstream raw materials:

(2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoic acid

(R)-3-phenyl-3-hydroxypropionic acid

phenylmethyl (R)-3-hydroxy-3-phenylpropanoate

(2S,3S)-3-Phenyl-oxirane-2-carboxylic acid

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