[(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester

Base Information

• Chemical Name: [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester
• CAS No.: 1058148-80-3
• Molecular Formula: C₂₅H₂₂FNO₄
• Molecular Weight: 419.452
• Mol file: 1058148-80-3.mol

Synonyms:[(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester

Chemical Property of [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester

There total 1 articles about [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl 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: 100.0%

O-benzyl-N-Fmoc-L-serine (122889-11-6,83792-48-7) → [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester (1058148-80-3)

Guidance literature:

With pyridine; trifluoro-[1,3,5]triazine; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.tet.2010.05.068

Reference yield: 86.0%

L-allylglycine (16338-48-0) + [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester (1058148-80-3) → Fmoc-L-Ser(OBn)-L-Agl-OH (1239278-27-3)

Guidance literature:

L-allylglycine; [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester; With sodium carbonate; In water; acetone; at 20 ℃; for 14h;

With hydrogenchloride; In dichloromethane; water; pH=2; Cooling with ice;

DOI:10.1016/j.tet.2010.05.068

Reference yield: 68.0%

tert-butyl [(1S,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (216260-41-2) + [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester (1058148-80-3) → C33H36N4O6 (1058148-50-7)

Guidance literature:

tert-butyl [(1S,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate; [(S)-2-benzyloxy-1-fluorocarbonylethyl]carbamic acid 9H-fluoren-9-yl-methyl ester; With 4-methyl-morpholine; In ethanol; at 20 ℃; for 0.25h;

With sodium acetate; In ethanol; for 3h; Further stages.; Heating;

DOI:10.1016/j.tetlet.2008.06.091

upstream raw materials:

O-benzyl-N-Fmoc-L-serine

Downstream raw materials:

C₃₃H₃₆N₄O₆

Fmoc-L-Ser(OBn)-L-Agl-OH

Refernces

• 1、 Van Lierop, Bianca J.,Jackson, W.Roy,Robinson, Andrea J.. "5,5-Dimethylproline dipeptides: Anacid-stable class of pseudoproline". experimental part. p. 5357 - 5366. Retrieved 2010/08/13.