(4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid | CAS No. 186023-49-4

(4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid

Basic Information

CAS Number

186023-49-4

Molecular Formula

C26H30N2O6

Molecular Weight

466.53 g/mol

AD

Basic Physical Properties

Solubility

Insuluble (1.6E-3 g/L) (25 ºC),

CC(C)[C@@H](C(=O)N1[C@@H](COC1(C)C)C(=O)O)NC(=O)OCC2c3ccccc3-c4c2cccc4

InChI

InChI=1S/C26H30N2O6/c1-15(2)22(23(29)28-21(24(30)31)14-34-26(28,3)4)27-25(32)33-13-20-18-11-7-5-9-16(18)17-10-6-8-12-19(17)20/h5-12,15,20-22H,13-14H2,1-4H3,(H,27,32)(H,30,31)/t21-,22-/m0/s1

InChIKey

KLYUTTJBDDHKOC-VXKWHMMOSA-N

LogP

3.597800000000001

Topological Polar Surface Area

105.17 Ų

Hydrogen Bond Donor/Acceptor

2 / 8

Synonyms & References

English

  • Fmoc-Val-Ser(Psi(Me,Me)pro)-OH
  • (S)-3-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanoyl)-2,2-dimethyloxazolidine-4-carboxylic acid
  • Fmoc-L-Val-L-Ser[PSI(Me,Me)Pro]-OH
  • Fmoc-Val-Ser(Psi(Me00Me)pro)-OH
  • Fmoc-Val-Ser{psi(Me,Me)pro}-OH
  • FMOC-VAL-SER(PSIME,MEPRO)-OH
  • Fmoc-Val-Ser[Ψ(Me,Me)Pro]-OH
  • (9H-Fluoren-9-yl)MethOxy]Carbonyl Val-SerPsi(Me,Me)Pro-OH
  • (S)-3-[N-(9-Fluorenylmethyloxycarbonyl)-L-valinyl]-2,2-dimethyloxazolidine-4-carboxylic acid
  • (4S)-3-[(2S)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-3-methyl-1-oxobutyl]-2,2-dimethyl-4-oxazolidinecarboxylic acid

MDL Number

MFCD18427720

FAQ

What are the physical and chemical properties of (4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (CAS: 186023-49-4)?

(4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid is a white crystalline solid with a molecular weight of approximately 513.4 g/mol. It has low water solubility and high solubility in organic solvents. The compound is known for its reactivity in peptide coupling reactions and can form stable esters and amides. It is stable under normal storage conditions but should be protected from moisture and heat.

How is (4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (CAS: 186023-49-4) typically synthesized?

(4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid is usually synthesized via the coupling of fluoren-9-ylmethanol with L-valine using a suitable coupling reagent such as HATU or DCC in the presence of a base like DIPEA. The reaction proceeds via a Michael addition followed by a coupling step to form the desired product.

What industries use (4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (CAS: 186023-49-4)?

(4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid is primarily used in the pharmaceutical industry for the synthesis of peptide-based drugs. It is also utilized in the production of certain types of polymers and as a building block for custom organic synthesis in academic and industrial research settings.

What precautions should be taken when handling (4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (CAS: 186023-49-4)?

When handling (4S)-3-{N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valyl}-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid, it is important to use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and laboratory coat. The substance should be handled in a well-ventilated area or a fume hood. In case of a spill, follow the manufacturer's safety data sheet (SDS) guidelines for cleanup. This compound is not highly reactive but should be protected from moisture and heat to maintain stability.

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