Fmoc-threo-beta-phenyl-Ser-OH

Base Information

• Chemical Name: Fmoc-threo-beta-phenyl-Ser-OH
• CAS No.: 487060-72-0
• Molecular Formula: C₂₄H₂₁NO₅
• Molecular Weight: 403.434
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20373288
• Nikkaji Number: J1.218.772F
• Wikidata: Q82161443
• Mol file: 487060-72-0.mol

Synonyms:Fmoc-threo-beta-phenyl-Ser-OH;487060-76-4;487060-72-0;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-phenylpropanoic acid;AC1MBT0F;(2R, 3S)/(2S, 3R)-Racemic Fmoc-beta-hydroxyphenylalanine;Fmoc-D-threo-3-Ph-Ser-OMe;SCHEMBL17703894;DTXSID20373288;CS-0210808;(2R, 3S)/(2S, 3R) - Racemic Fmoc - beta - hydroxyphenylalanine

Chemical Property of Fmoc-threo-beta-phenyl-Ser-OH

Chemical Property:

• PSA: 95.86000
• LogP: 4.10280
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 403.14197277
• Heavy Atom Count: 30
• Complexity: 582

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-threo-beta-phenylserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O

Technology Process of Fmoc-threo-beta-phenyl-Ser-OH

There total 28 articles about Fmoc-threo-beta-phenyl-Ser-OH 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:

(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) → Fmoc-threo-β-OH-L-Phe-OH (197458-39-2,487060-72-0)

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

upstream raw materials:

(2S,3R)-3-phenylserine

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

(fluorenylmethoxy)carbonyl chloride

dl-threo-phenylserine