Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid

Base Information

• Chemical Name: Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid
• CAS No.: 583827-12-7
• Molecular Formula: C₂₅H₂₉N₂O₅
• Molecular Weight: 437.516
• Mol file: 583827-12-7.mol

Synonyms:

Chemical Property of Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A protected spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state.

Technology Process of Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid

There total 5 articles about Fmoc-(3S,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid 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: 40.0%

(3R,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid methyl ester (864150-31-2) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (3R,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2,2,6,6-tetramethylpiperidine-1-oxyl-3-carboxylic acid (864150-33-4,583827-12-7)

Guidance literature:

(3R,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid methyl ester; With sodium hydroxide; In methanol; water; for 5h; Heating;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium hydrogencarbonate; In water; acetone; at 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2005.06.049

Reference yield:

(3R,4S)-4-[(1'S)-phenylethyl]amino-3-methoxycarbonyl-2,2,6,6-tetramethyl-piperidine-1-oxyl hydrochloride (583827-08-1,583827-06-9) → (3R,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2,2,6,6-tetramethylpiperidine-1-oxyl-3-carboxylic acid (864150-33-4,583827-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: H₂ / Pd/C / ethanol / 0.33 h

1.2: 41 percent / copper(II) acetate / methanol / 168 h

2.1: NaOH / methanol; H₂O / 2 h / 75 °C

2.2: 40 percent / NaHCO₃ / methanol; H₂O; acetone / 18 h / 20 °C

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; ethanol; water;

DOI:10.1002/ejoc.200700153

Reference yield:

2,2,6,6-tetramethyl-3-methoxycarbonyl-4-piperidone-1-oxyl (77874-89-6) → (3R,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2,2,6,6-tetramethylpiperidine-1-oxyl-3-carboxylic acid (864150-33-4,583827-12-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / 4A MS / ethanol; acetic acid / 48 h / 20 °C

2.1: 30 percent / isobutyric acid; NaBH₄ / toluene / 20 h

3.1: H₂ / Pd/C / ethanol / 0.33 h

3.2: 41 percent / copper(II) acetate / methanol / 168 h

4.1: NaOH / methanol; H₂O / 2 h / 75 °C

4.2: 40 percent / NaHCO₃ / methanol; H₂O; acetone / 18 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; hydrogen; isobutyric Acid; palladium on activated charcoal; In methanol; ethanol; water; acetic acid; toluene;

DOI:10.1002/ejoc.200700153

upstream raw materials:

(3R,4S)-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid methyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3R,4S)-4-[(1'S)-phenylethyl]amino-3-methoxycarbonyl-2,2,6,6-tetramethyl-piperidine-1-oxyl hydrochloride

(3S,4S)-4-[(1'S)-phenylethyl]amino-3-methoxycarbonyl-2,2,6,6-tetramethyl-piperidine-1-oxyl hydrochloride