68756-64-9

Usage

InChI:InChI=1/C7H14O3/c1-3-4-5-6(8)7(9)10-2/h6,8H,3-5H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 636-36-2 rac-2-hydroxyhexanoic acid 
• 84393-11-3 <<(α-methoxy)hex-1-enyl>oxy>trimethylsilane 
• 61603-67-6 1,1,1-tris(methylthio)-2-hexanol 
• 865-34-9 lithium methanolate 
• 67-56-1 methanol 
• 64350-07-8 2-hydroxyhexanenitrile 
• 2396-77-2 methyl 2-hexenoate 
• 110-62-3 pentanal 
• 133842-19-0 C₁₃H₂₈O₄Si 

Downstream Products

• 110320-68-8 methyl 2-benzyloxyhexanoate 
• 66832-04-0 methyl 6-benzyloxy-5-hydroxy-3-oxodecanoate 
• 54620-78-9 6-(1'-benzyloxypentyl)-5,6-dihydro-4-methoxypyran-2-one 
• 136850-73-2 6-(1'-benzyloxypentyl)-5,6-dihydropyran-2,4(3H)-dione 
• 34565-32-7 (+/-) epi-pestalotin 
• 141554-36-1 2-(benzyloxy)hexan-1-ol 
• 106225-84-7 2-(1'-benzyloxypentyl)-2,3-dihydro-6-methoxypyran-4-one 
• 54620-78-9 6-(1'-benzyloxypentyl)-5,6-dihydro-4-methoxypyran-2-one 
• 70326-39-5 α-benzyloxyhexanal 

Relevant academic research and scientific papers

Synthesis method 2- hydroxyl carboxylic ester (by machine translation)

The method, is simple 2 - energy consumption, energy consumption is low, the production :(1) of waste water can be greatly reduced, the yield of the target product is high 2 - and the production cost ;(2) is greatly reduced (1). 2 - The method comprises the following steps, preparing 2 - hydroxycarboxylate, with an acid ;(3) by a byproduct ammonium salt (2) in step, and filtering the excess acid, to remove the byproduct ammonium salt, to obtain 2 - hydroxyl carboxylic acid ester product, by esterification reaction in step (, and filtering to remove 2 - the excess, alcohol), from, the reaction, solution obtained by the reaction solution; of the catalyst under the, action of, a catalyst, to obtain the product of the compound. (by machine translation)

Preparation method of 2-hydroxy acid ester

The invention relates to a preparation method of 2-hydroxy acid ester and belongs to the technical field of organic synthesis. According to the preparation method of 2-hydroxy acid ester, 2-hydroxy alkyl cyanogens is taken as a raw material to be added to a reaction solution formed by hydrogen chloride, alcohol and water, and after reaction, 2-hydroxy acid ester is obtained. According to the preparation method of 2-hydroxy acid ester, use of a large amount of nonpolar solvent is not needed, and a target product can be obtained by a one-pot method, thus lowering production cost, improving production efficiency and the purify of the target product, and having energy-saving and environment-friendly effects.

Asymmetric transfer hydrogenation of α-azido acrylates

The asymmetric transfer hydrogenation of α-azido acrylates has been explored, a range of α-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A.

Biocatalytic racemization of α-hydroxycarboxylic acids using a stereo-complementary pair of α-hydroxycarboxylic acid dehydrogenases

Biocatalytic racemization of aliphatic, (aryl)aliphatic and aromatic α-hydroxycarboxylic acids was achieved via a reversible oxidation-reduction sequence using a pair of stereo-complementary Prelog- and anti-Prelog d- and l-α-hydroxyisocaproate dehydrogenases from Lactobacillus confusus DSM 20196 and Lactobacillus paracasei DSM 20008, resp., overexpressed in Escherichia coli. The mild reaction conditions ensured essential 'clean' isomerization, undesired 'over-oxidation' of the substrate forming the α-ketoacid could be suppressed by exclusion of O2 and adjustment of the NAD+/NADH-ratio.

PROCESS FOR PRODUCTION OF 2-HYDROXY ESTERS

The invention provides an easy and simple process for the production of 2-hydroxy esters from cyanohydrins, specifically, a process for the production of 2-hydroxy esters represented by the general formula (1) (exclusive of ethyl 2-hydroxy-4-phenylbutyrate), characterized by introducing an acid into a mixture comprising a cyanohydrin represented by the general formula (2), an alcohol, an organic solvent and water: [Chemical formula 1] R1 -CH(OH)-COOR2 (1) R1 -CH(OH)(CN) (2) wherein R1 is hydrogen, a substituted or unsubstituted aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, a substituted or unsubstituted alicyclic hydrocarbon group which has 3 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, or a substituted or unsubstituted aryl or aralkyl group which has 3 to 14 carbon atoms and may contain oxygen, sulfur, or nitrogen; and R2 is alkyl which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen.

Bromolysis and iodolysis of α,β-epoxycarboxylic acids in water catalyzed by indium halides

The ring opening of α,β-epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-β-monoalkylated epoxycarboxylic acids at pH 4.0 was completely α-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of α,β-epoxycarboxylic acids at pH 1.5 gave the corresponding anti β-iodohydrins in 88-95% yields. The one-pot synthesis of the α- and β-hydroxyhexanoic acids, starting from the corresponding α,β-epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.

Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes

Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic α-hydroxyaldehydes 7 (R1=Et, Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses ≥93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses ≤78%.

Oxidation of α-acetoxy acetals with trichloroisocyanuric acid

α-Acetoxy acid methyl esters are prepared in excellent yields by treating aliphatic α-acetoxy dimethyl acetals with trichloroisocyanuric acid in DMF.

High Diastereoselection in the Aldol Reaction of the Bistrimethylsilyl Enol Ether of Methyl Acetoacetate with 2-Benzyloxyhexanal: Synthesis of (-)-Pestalotin

Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride.The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.

Oxygenation of Silyl Enol Ethers and Silyl Ketene Acetals with Molecular Oxygen and Aldehyde Catalyzed by Nickel(II) Complex. A Convenient Method for the Preparation of α-Hydroxy Carbonyl Compounds

In the presence of a catalytic amount of nickel(II) complex, silyl enol ethers and silyl ketene acetals are smoothly oxygenated by the combined use of molecular oxygen and aldehyde to afford α-siloxy carbonyl compounds via possible intermediates, siloxy epoxides.And on treatment of the α-siloxy carbonyl compounds with potassium fluoride α-hydroxy carbonyl compounds are obtained in good to high yields.