[(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

Base Information

• Chemical Name: [(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
• CAS No.: 206191-20-0
• Molecular Formula: C₃₀H₃₁NO₇
• Molecular Weight: 517.579
• Mol file: 206191-20-0.mol

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 7 articles about [(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 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:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → [(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:

Multi-step reaction with 5 steps

1: 92 percent / NaBr / acetone / 30 h / Heating

2: 1.) Cs₂CO₃ / 1.) H₂O, 20 min, 2.) DMF, room temperature, 24 h

3: 1.) BF₃*Et₂O, 2.) TEA / 1.) CH₂Cl₂, 0 deg C to room temperature, 6 h, 2.) 30 min

4: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) -78 deg C, 30 min; 0 deg C, 10 min

5: diethyl ether / 25 °C

With oxalyl dichloride; TEA; boron trifluoride diethyl etherate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium bromide; In diethyl ether; acetone;

DOI:10.1021/jo972294l

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → [(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:

Multi-step reaction with 4 steps

1: 1.) Cs₂CO₃ / 1.) H₂O, 20 min, 2.) DMF, room temperature, 24 h

2: 1.) BF₃*Et₂O, 2.) TEA / 1.) CH₂Cl₂, 0 deg C to room temperature, 6 h, 2.) 30 min

3: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) -78 deg C, 30 min; 0 deg C, 10 min

4: diethyl ether / 25 °C

With oxalyl dichloride; TEA; boron trifluoride diethyl etherate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In diethyl ether;

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

upstream raw materials:

4-methoxyphenyl magnesium bromide

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

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

3-bromomethyl-3-methyloxetane

Downstream raw materials:

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