65635-85-0

Basic information

• Product Name: Cbz-N-Methyl-D-leucine
• Synonyms: Cbz-N-Methyl-D-leucine;Cbz-N-Me-D-Leu-OH;(R)-2-(((Benzyloxy)carbonyl)(methyl)amino)-4-methylpentanoic acid
• CAS NO: 65635-85-0
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33154
• Mol File: 65635-85-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Cbz-N-Methyl-D-leucine(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-N-Methyl-D-leucine(65635-85-0)
• EPA Substance Registry System: Cbz-N-Methyl-D-leucine(65635-85-0)

Safety Data

• Hazardous Substances Data: 65635-85-0(Hazardous Substances Data)

Usage

Description

Cbz-N-Methyl-D-leucine is a chemical compound derived from N-methyl-D-leucine, an amino acid. It is a white to off-white crystalline powder with a molecular weight of 219.27 g/mol. The chemical structure of Cbz-N-Methyl-D-leucine consists of a carbobenzyloxy (Cbz) protecting group attached to the N-methyl-D-leucine amino acid. Cbz-N-Methyl-D-leucine is soluble in organic solvents such as methanol and dichloromethane.

Uses

Used in Pharmaceutical Research:
Cbz-N-Methyl-D-leucine is used as a building block in the creation of novel drug candidates. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals.
Used in Peptide Synthesis:
Cbz-N-Methyl-D-leucine is used as a protecting group for amino acids during the chemical synthesis process. This prevents unwanted reactions and allows for the controlled formation of peptide bonds, which is crucial for the synthesis of complex peptide structures.
Used in Chemical Synthesis:
Cbz-N-Methyl-D-leucine is used as a protecting group in various chemical synthesis processes. Its carbobenzyloxy (Cbz) group can be selectively removed under mild conditions, allowing for the controlled formation of desired products without affecting other functional groups in the molecule.

Upstream product

• 328-38-1 (R)-leucine 
• 28862-79-5 Z-D-Leu-OH 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 129919-93-3 N-<(benzyloxy)carbonyl>-N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester 
• 120448-64-8 -threonine methyl ester 
• 128892-35-3 Z-D-MeLeu-MeVal-OMe 
• 110720-12-2 N-Z-didemnin A 
• 127526-57-2 (R)-2-[(R)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-3-(3,5-dichloro-4-hydroxy-phenyl)-propionic acid 
• 110720-26-8 Z-D-MeLeu-Thr-OTMSe 
• 120286-06-8 Z-(R)-MeLeu-SPY 
• 117710-30-2 N-(benzyloxycarbonyl)-N-methyl-D-leucine methyl ester 
• 187328-69-4 {[(R)-2-(Benzyloxycarbonyl-methyl-amino)-4-methyl-pentanoyl]-methyl-amino}-acetic acid tert-butyl ester 
• 187328-70-7 ({(R)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-4-methyl-pentanoyl}-methyl-amino)-acetic acid tert-butyl ester 
• 77327-04-9 Didemnin A 
• 120286-05-7 Cyclo<(N-L-prolyl-N-methyl-D-leucyl)-O-<oxy>-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> 
• 161708-48-1 C₆₂H₉₁N₇O₁₆ 
• 161708-41-4 N-Cbz-3,4-didehydro-L-prolyl-N-methyl-D-leucine 

Relevant articles and documents

Synthesis of dysideaproline e using organocatalysis

(S)-4,4-Dichloro-3-methylbutanoic acid was prepared in 51% overall yield from commercially available starting materials using an organocatalytic transfer hydrogenation to 4,4-dichloro-3-methylbut-2-enal in the key step. The (S)-dichloro acid was used as an intermediate in the first total synthesis of dysideaproline E and a diastereomer confirming the structure of the natural product.

Synthesis of new didemnin B analogs for investigations of structure/biological activity relationships

Modifications were introduced in the side chain of didemnin B to afford several analogs (1f-1j) for biological testing in order to identify the features responsible for the bioactivity of the natural products (1a-1c). To achieve our goal, two changes were made in the proline ring of the b-turn side chain. Initially, a hydroxyl group was incorporated at the C-4 position of the ring to increase the polar nature of the molecule. Secondly, unsaturation was introduced at C-3 and C-4 to increase the rigidity of the ring and to provide a site for tritiation to follow the drug pathway in biological systems. Improvements were also introduced in the macrocycle construction to produce gram quantities of this unit (1d) for the preparation of the planned analogs. The linear precursor to the macrocycle was oxidized more effectively with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane reagent), and cyclization yields were increased substantially by using a new coupling reagent, pentafluorophenyl diphenylphosphinate (FDPP). (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and pentafluorophenyl trifluoroacetate were also used to improve other coupling reactions.