1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Base Information

• Chemical Name: 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS No.: 206191-13-1
• Molecular Formula: C₃₀H₂₉NO₇
• Molecular Weight: 515.563
• Mol file: 206191-13-1.mol

Synonyms:

Chemical Property of 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

There total 1 articles about 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 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:

[(S)-2-Hydroxy-2-(4-methoxy-phenyl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester → 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-13-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) -78 deg C, 30 min; 0 deg C, 10 min;

DOI:10.1021/jo972294l

Reference yield:

1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-13-1) → [(1S,2R)-2-Hydroxy-2-(4-methoxy-phenyl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester + [(1S,2S)-2-Hydroxy-2-(4-methoxy-phenyl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (206191-20-0)

Guidance literature:

With lithium borohydride; In methanol; dichloromethane; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo972294l

Reference yield:

1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (206191-13-1) → (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid (153829-66-4)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / CH₂Cl₂; methanol / -78 °C

2: 1.) piperidine, 2.) TFA, 3.) Cs₂CO₃ / 2.) H₂O, 3.) H₂O

With piperidine; lithium borohydride; caesium carbonate; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1021/jo972294l

Downstream raw materials:

[(1S,2S)-2-Hydroxy-2-(4-methoxy-phenyl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

(2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid