1596360-03-0

Basic information

• Product Name: (1S,2S,5R)-2-amino-5-isopropylcyclopentane-1-carboxylic acid
• CAS NO: 1596360-03-0
• Molecular Weight: 171.239
• Mol File: 1596360-03-0.mol

Chemical Properties

• CAS DataBase Reference: (1S,2S,5R)-2-amino-5-isopropylcyclopentane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R)-2-amino-5-isopropylcyclopentane-1-carboxylic acid(1596360-03-0)
• EPA Substance Registry System: (1S,2S,5R)-2-amino-5-isopropylcyclopentane-1-carboxylic acid(1596360-03-0)

Safety Data

• Hazardous Substances Data: 1596360-03-0(Hazardous Substances Data)

Upstream product

• 328239-96-9 5-hydroxycyclopent-1-enecarboxylic acid methyl ester 
• 1596359-94-2 methyl (1S,2S,5R)-2-amino-5-isopropylcyclopentane-1-carboxylate 
• 1596359-88-4 methyl (S,S,S,S)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-isopropylcyclopent-3-ene-1-carboxylate 

Relevant articles and documents

The asymmetric synthesis of enantiopure C(5)-substituted transpentacins via diastereoselective conjugate additions to a β′-amino-α,β-unsaturated ester

The asymmetric synthesis of a range of 1,2-anti-1,5-syn-transpentacins, bearing either alkyl, phenyl or hydroxymethyl substituents at the C(5)-position, has been achieved using the diastereoselective conjugate additions of Grignard reagents to an enantiopure β′-amino-α,β-unsaturated ester as the key step. In addition, the doubly diastereoselective conjugate addition of an enantiopure lithium amide reagent to the β′-amino-α,β-unsaturated ester provided access to the corresponding β,β′-diamino ester, which was subsequently converted to both (S,S)-(2,5-diaminocyclopent-1-yl)methanol and (S,S)-2,5-diaminocyclopentane-1-carboxylic acid. In each case, the final enantiopure products were obtained as single diastereoisomers (>99:1 dr) in good yields over five steps or fewer from commercially available starting materials.

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.