69901-75-3

Basic information

• Product Name: Cbz-Cyclohexyl-L-glycine
• Synonyms: Z-CHG-OH;Z-CYCLOHEXYL-GLY-OH;Z-L-2-CYCLOHEXYLGLYCINE;Z-L-CYCLOHEXYLGLYCINE;Z-PHG(HEXAHYDRO)-OH;(S)-CBZ-CYCLOHEXYLGLYCINE;N-ALPHA-CARBOBENZOXY-L-CYCLOHEXYLGLYCINE;N-ALPHA-CARBOBENZOXY-HEXAHYDRO-L-PHENYLGLYCINE
• CAS NO: 69901-75-3
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.34
• Product Categories: chiral;Chiral Reagent;Amino Acids & Derivatives;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 69901-75-3.mol

Chemical Properties

• Melting Point: 111-114°C
• Boiling Point: 492.1 °C at 760 mmHg
• Flash Point: 251.4 °C
• Appearance: White/Solid
• Density: 1.2 g/cm³
• Vapor Pressure: 1.68E-10mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.99±0.10(Predicted)
• CAS DataBase Reference: Cbz-Cyclohexyl-L-glycine(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-Cyclohexyl-L-glycine(69901-75-3)
• EPA Substance Registry System: Cbz-Cyclohexyl-L-glycine(69901-75-3)

Safety Data

• Hazardous Substances Data: 69901-75-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cbz-Cyclohexyl-L-glycine is used as a building block for the synthesis of peptides that act as inhibitors of serine proteases. Its primary application is in the development of treatments targeting the hepatitis C virus NS3-NS4A protease, which plays a crucial role in the viral replication process.
The use of Cbz-Cyclohexyl-L-glycine in the pharmaceutical industry is driven by its potential to contribute to the creation of effective antiviral therapies against hepatitis C, a viral disease that affects millions of people worldwide. By inhibiting the NS3-NS4A protease, these peptides can disrupt the virus's life cycle and help in the development of novel treatment strategies.

InChI:InChI=1/C16H21NO4/c18-15(19)14(13-9-5-2-6-10-13)17-16(20)21-11-12-7-3-1-4-8-12/h1,3-4,7-8,13-14H,2,5-6,9-11H2,(H,17,20)(H,18,19)/t14-/m0/s1

Upstream product

• 621-84-1 O-benzyl carbamate 
• 4354-49-8 2-cyclohexyl-2-oxoethanoic acid 
• 14328-51-9 (2S)-amino(cyclohexyl)ethanoic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1334324-63-8 ((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid benzyl ester 
• 615583-07-8 C₃₅H₅₃N₃O₆ 
• 143915-12-2 ((S)-1-Cyclohexyl-2-oxo-ethyl)-carbamic acid benzyl ester 
• 143914-85-6 (E)-(S)-4-Benzyloxycarbonylamino-4-cyclohexyl-2-methyl-but-2-enoic acid ethyl ester 
• 850251-49-9 C₃₁H₄₇N₃O₇ 
• 926276-17-7 (1S,3aR,6aS)-t-butyl 2-((S)-2-((S)-2-(benzyloxycarbonylamino)-2-cyclohexylacetamido)-3,3-dimethylbutanoyl)octahydrocyclopenta[c]pyrrole-1-carboxylate 
• 688735-01-5 (S)-tert-butyl 2-amino-2-cyclohexylacetate 

Relevant articles and documents

PROCESS FOR PRODUCING N-PROTECTED AMINO ACID

The present invention relates to a method for producing N-protected amino acid. Specifically, the present invention provides a method in which a protecting group is introduced to the amino group of an amino acid in a reaction under alkaline condition, and the N-protected amino acid thus generated is then separated from the reaction solution as crystals, without undergoing an extraction step or a concentration step. The present inventors have completed the invention based on the finding that desirable crystals of N-protected amino acids may be obtained without extraction, concentration or recrystallization steps between the initial generation of the N-protected amino acid molecules and the subsequent separation of the crystals, by first adding an water-soluble organic solvent and optionally water to the reaction solution (alkaline) containing the N-protected amino acid, and then neutralizing the solution by an acid.

Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor

(Chemical Equation Presented) A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-α-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.