500593-45-3

Usage

General Description

1,3-Cyclopentanedimethanol,4-amino-,(1R,3R,4R)-rel-(9CI) is a chemical compound that is also known as 4-amino-1,3-cyclopentanediol. It is a derivative of cyclopentanediol, which is a type of alcohol. 1,3-Cyclopentanedimethanol,4-amino-,(1R,3R,4R)-rel-(9CI) has a unique stereochemistry, as indicated by the (1R,3R,4R)-rel designation. It is used in the synthesis of other organic compounds and has potential applications in pharmaceuticals, materials science, and other industries. The chemical structure and properties of 1,3-Cyclopentanedimethanol,4-amino-,(1R,3R,4R)-rel-(9CI) make it a versatile building block for various chemical reactions and processes. Its stereochemistry also makes it a valuable tool for studying chiral chemical reactions and mechanisms.

Upstream product

• 1026064-90-3 C₁₁H₁₇NO₆ 
• 153759-54-7 (1R,2R,4R)-2,4-Bis(acetoxymethyl)cyclopentane-1-carboxamide 
• 1025944-54-0 (1R,2R,4S)-2-Carbamoyl-4-hydroxymethyl-cyclopentanecarboxylic acid 
• 1027145-85-2 (1R,2R,4R)-2,4-Bis-hydroxymethyl-cyclopentanecarboxylic acid amide 
• 153759-55-8 (1R,2R,4R)-2,4-Bis(acetoxymethyl)-1-<(tert-butoxycarbonyl)amino>cyclopentane 

Relevant academic research and scientific papers

Synthesis of Carbocyclic 2',3'-Dideoxy-2'-C-hydroxymethyl Nucleosides as Potential Inhibitors of HIV

The synthesis of the enantiomerically pure carbocyclic 2',3'-dideoxy-2'-C-hydroxymethyl derivatives of adenosine and guanosine is described. trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (4) was reacted with the zinc-dibromomethane-titanium tetrachloride mixed reagent to give an exocyclic olefin.Hydroboration followed by oxidation gave the C-2 symmetric hydroxymethyl diester 6.The two ester groups in 6 were differentiated by lactonization to give lactone 7.The lactone 7 was opened with ammonia, and the remaining carboxylic acid group was reduced.Hofmann rearrangement of the amide gave (1R,2R,4R)-2,4-bis(acetoxymethyl)-1-cyclopentane (9), which after deprotection was converted to the adenosine derivative 12 and the guanosine derivative 15.Compounds 12 and 15 were evaluated for activity against human immunodeficiency virus (HIV).

Divergent synthesis of two precursors of 3′-homo-2′-deoxy- and 2′-homo-3′-deoxy-carbocyclic nucleosides

Aminocyclopentanedimethanols 4 and 5, which are of interest for the synthesis of higher homologues of 2′-deoxy- and 3′-deoxycarbonucleosides, respectively, were efficiently prepared by divergent routes starting from (±)-exo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde. In the key step, ammonolysis of the common intermediate (±)-(1β,3β,4α)-4-benzoyloxymethyl-1,3- cyclopentanedicarboxylic anhydride and subsequent esterification afford near-equimolar amounts of two easily separable isomeric carbamoyl esters.