156406-14-3

Basic information

• Product Name: Cyclopentanecarboxylic acid, 2-amino-5-methyl-, (1alpha,2alpha,5beta)- (9CI)
• Synonyms: Cyclopentanecarboxylic acid, 2-amino-5-methyl-, (1alpha,2alpha,5beta)- (9CI)
• CAS NO: 156406-14-3
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.18362
• Product Categories: AMINOACID
• Mol File: 156406-14-3.mol

Chemical Properties

• Boiling Point: 266.1±33.0 °C(Predicted)
• Appearance: /
• Density: 1.114±0.06 g/cm3(Predicted)
• PKA: 3.88±0.40(Predicted)
• CAS DataBase Reference: Cyclopentanecarboxylic acid, 2-amino-5-methyl-, (1alpha,2alpha,5beta)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanecarboxylic acid, 2-amino-5-methyl-, (1alpha,2alpha,5beta)- (9CI)(156406-14-3)
• EPA Substance Registry System: Cyclopentanecarboxylic acid, 2-amino-5-methyl-, (1alpha,2alpha,5beta)- (9CI)(156406-14-3)

Safety Data

• Hazardous Substances Data: 156406-14-3(Hazardous Substances Data)

Upstream product

• 1046428-08-3 methyl (1S,2R,5R)-2-amino-5-methylcyclopentanecarboxylate trifluoroacetic acid salt 
• 1448055-11-5 C₂₅H₃₁NO₂ 
• 1448055-15-9 methyl (S,S,S,S,E)-2-(but-3'-en-2'-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 1448055-22-8 methyl (S,S,S,S)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopent-3-ene-1-carboxylate 
• 1448055-24-0 methyl (S,S,S)-2-amino-5-methylcyclopentane-1-carboxylate 

Relevant articles and documents

Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: Applications in the asymmetric synthesis of C(5)-substituted transpentacins

The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials. This journal is the Partner Organisations 2014.

Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland-Claisen rearrangements

Asymmetric syntheses of (S,S,S)-2-amino-5-methylcyclopentanecarboxylic acid and (S,S,S)-2-amino-5-phenylcyclopentanecarboxylic acid were achieved in 9 steps from commercially available starting materials via the Ireland-Claisen rearrangement of two enanti

Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee.