110611-68-2

Basic information

• Product Name: ethyl trans-2-hydroxy-1-cyclopentane carboxylate
• CAS NO: 110611-68-2
• Molecular Weight: 158.197
• Mol File: 110611-68-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: ethyl trans-2-hydroxy-1-cyclopentane carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl trans-2-hydroxy-1-cyclopentane carboxylate(110611-68-2)
• EPA Substance Registry System: ethyl trans-2-hydroxy-1-cyclopentane carboxylate(110611-68-2)

Safety Data

• Hazardous Substances Data: 110611-68-2(Hazardous Substances Data)

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 294212-87-6 ethyl 2-bromo-6-oxohexanoate 
• 1092929-40-2 (Z)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 13038-15-8 (E)-6-hydroxy-hex-2-enoic acid ethyl ester 
• 124668-80-0 (E)-ethyl 6-[(methylsulfonyl)oxy]hex-2-enoate 
• 5299-60-5 6-hydroxy-hexanoic acid ethyl ester 
• 294212-80-9 2-bromo-6-triethylsilanyloxy-hexanoic acid ethyl ester 
• 294212-79-6 ethyl 6-triethylsilyloxyhexanoate 
• 294212-81-0 ethyl 2-bromo-6-hydroxyhexanoate 
• 63578-04-1 (+/-)-trans-2-(3.5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 63578-04-1 (+/-)-cis-2-(3,5-dinitro-benzoyloxy)-cyclopentane-carboxylic acid-⁽¹⁾-ethyl ester 
• 186581-53-3 diazomethane 
• 108-05-4 vinyl acetate 
• 1883-91-6 ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate 

Downstream Products

• 130023-71-1 (+/-)-cis-2-hydroxy-cyclopentane-carboxylic acid-⁽¹⁾-hydrazide 
• 130023-71-1 (+/-)-trans-2-hydroxy-cyclopentane-carboxylic acid-⁽¹⁾-hydrazide 
• 86984-42-1 (4aS,7aS)-3-Methyl-hexahydro-cyclopenta[e][1,3]oxazin-2-one 
• 86984-42-1 (4aR,7aS)-3-Methyl-hexahydro-cyclopenta[e][1,3]oxazin-2-one 
• 169868-13-7 (1S,2R)-2-hydroxycyclopentane-1-carboxylic acid 
• 61586-79-6 ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate 
• 124150-23-8 (1R,2S)-2-methoxycarbonylcyclopentan-1-ol 
• 122331-03-7 ethyl (1S,2S)-2-hydroxycyclopentanecarboxylate 
• 110611-67-1 ethyl (1R,2R)-2-hydroxycyclopentanecarboxylate 

Relevant articles and documents

Lipase-catalysed resolution of cyclic cis- and trans-β-hydroxy esters

Lipases A and B from Candida antarctica are shown to be highly efficient and complementary biocatalysts for the resolution of five- to seven-membered cyclic β-hydroxy esters by O-acylation. Using this procedure, all four stereoisomers of each one are obtained in enantiopure form and very high yields.

Chemo-enzymatic synthesis of (R)-5-hydroxymethyl-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethylsulfonate, a potential chiral building block for multicyclic terpenoids

The chemo-enzymatic synthesis of (R)-5-hydroxymethyl-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethylsulfonate, a potential chiral building block for polycyclic terpenoids containing a five–membered ring having isopropyl and angular methyl substituents, such as erinacin A and dolatriol, was achieved over 11 steps from ethyl 2-oxocyclopentane-1-carboxylate. The key synthetic precursor for this triflate was ethyl (1S,2R)-2-hydroxycyclopentanecarboxylate (>99% ee), which was prepared by a lipase-catalyzed enantioselective hydrolysis of the corresponding racemic acetate. The antipodal (S)-triflate is expected to be the synthetic intermediate for another group of terpenoids involving hamigeran B and stolonidiol. Enantiomerically pure (1R,2S)-hydroxyester (>99% ee) was prepared in high yield using the asymmetric reduction of the oxoester with commercially available carbonyl reductase, “Chiralscreen OH”-E001.

Immobilized baker's yeast reduction of ketones in an ionic liquid, [bmim]PF6 and water mix

The bioreduction with immobilized baker's yeast of several ketones was carried out in a 10:1 [bmim]PF6 ionic liquid/water mix. The reductions produced alcohols with comparable enantioselectivities to baker's yeast reductions in alternative media.

Investigation of Electrostatic Interactions towards Controlling Silylation-Based Kinetic Resolutions

Electrostatic interactions between a silylated isothiourea intermediate and an ester π system were explored by determining how variations in sterics and electronics affect the selectivity of a silylation-based kinetic resolution. Sterics on the π systems affect the selectivity factors of alkyl 2-hydroxycyclohexanecarboxylates, resulting in a strong correlation of selectivity factors to Charton values. Induction effects of electron-withdrawing substituents on phenyl esters significantly enhance selectivity supporting an edge to face π–π interaction. The linear free energy relationships that were uncovered will aid in future incorporation of intermolecular electrostatic interactions towards controlling asymmetric reactions.

A recombinant ketoreductase tool-box. Assessing the substrate selectivity and stereoselectivity toward the reduction of β-ketoesters

The substrate selectivity and stereoselectivity of a series of ketoreductases were evaluated toward the reduction of two sets of β-ketoesters. Both the structural variety at β-position and the substituent at α-position greatly affected the activity and stereoselectivity of these ketoreductases. For the first set of β-ketoesters, at least one ketoreductase was found that catalyzed the formation of either (d) or (l) enantiomer of β-hydroxyesters from each substrate with high optical purity, with the only exception of ethyl (d)-3-hydroxy-3-phenylpropionate. For the second set of β-ketoesters with α-substituents, the situation is more complex. More commonly, a ketoreductase was found that formed one of the four diastereomers in optically pure form, with only a few cases in which enzymes could be found that formed two or more of the diastereomers in high optical purity. The continued development of new, more diverse ketoreductases will create the capability to produce a wider range of single diastereomers of 2-substituted-3-hydroxy acids and their derivatives.