(2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid

Base Information

• Chemical Name: (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid
• CAS No.: 487060-76-4
• Molecular Formula: C₂₄H₂₁NO₅
• Molecular Weight: 403.434
• Mol file: 487060-76-4.mol

Synonyms:(2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid

Chemical Property of (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid

There total 6 articles about (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic 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:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + dl-threo-phenylserine (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0) → Fmoc-threo-β-OH-L-Phe-OH (197458-39-2,487060-72-0) + (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid (487060-76-4,487060-72-0)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 1h;

DOI:10.1021/jo0303113

Reference yield:

dl-threo-phenylserine (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0) → (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid (487060-76-4,487060-72-0)

Guidance literature:

Multi-step reaction with 5 steps

1: HCl / 18 h / 5 - 20 °C

2: aq. AcONa / 16 h / 5 - 20 °C

3: bovine pancreas α-chymotrypsin II; 0.05 aq. phosphate buffer / 20 h / 20 °C / pH 8

4: 6 M aq. HCl / 5 h / Heating

5: aq. Na₂CO₃ / tetrahydrofuran / 5 h

With hydrogenchloride; phosphate buffer; bovine pancreas α-chymotrypsin II; sodium acetate; sodium carbonate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00508-5

Reference yield:

methyl (2R,3S)-threo-N-acetyl-β-phenylserinate (255896-85-6) → (2R,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenyl-propionic acid (487060-76-4,487060-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 6 M aq. HCl / 5 h / Heating

2: aq. Na₂CO₃ / tetrahydrofuran / 5 h

With hydrogenchloride; sodium carbonate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00508-5

upstream raw materials:

(2R,3S)-phenylserine

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

(fluorenylmethoxy)carbonyl chloride

dl-threo-phenylserine

Downstream raw materials:

threo-(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride