(3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate

Base Information

• Chemical Name: (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate
• CAS No.: 1312681-99-4
• Molecular Formula: C₃₂H₃₂N₂O₆
• Molecular Weight: 540.616
• Mol file: 1312681-99-4.mol

Synonyms:

Chemical Property of (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate

There total 5 articles about (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate 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: 53.0%

(3S,6R,7S,10S)-methyl 2-oxo-3-N-(9-fluorenylmethoxycarbonyl)amino-6-iodo-1-azabicyclo[5.3.0]decane-10-carboxylate + phenol (108-95-2,27073-41-2) → (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate (1312681-99-4)

Guidance literature:

With silver trifluoromethanesulfonate; at 50 ℃; Inert atmosphere;

DOI:10.1021/jo2006363

Reference yield:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid (851909-08-5) → (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate (1312681-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / Inert atmosphere; Reflux

3: iodine; sodium hydrogencarbonate / acetonitrile / 0.33 h / 20 °C / Inert atmosphere

4: silver trifluoromethanesulfonate / 50 °C / Inert atmosphere

With Grubbs catalyst first generation; iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo2006363

Reference yield:

homoallylglycine methyl ester trifluoroacetate → (3S,6R,7S,10S)-methyl 2-oxo-3-N-(Fmoc)amino-6-phenoxy-1-azabicyclo[5.3.0]decane-10-carboxylate (1312681-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / Inert atmosphere; Reflux

3: iodine; sodium hydrogencarbonate / acetonitrile / 0.33 h / 20 °C / Inert atmosphere

4: silver trifluoromethanesulfonate / 50 °C / Inert atmosphere

With Grubbs catalyst first generation; iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo2006363

upstream raw materials:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hex-5-enoic acid

(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-hex-5-enoylamino]-hex-5-enoic acid methyl ester

phenol