76835-66-0

Upstream product

• 186581-53-3 diazomethane 
• 28254-78-6 (3R)-(-)-3-Hydroxydodecanoic acid 
• 76835-64-8 methyl 3-oxododecanoate 
• 61058-75-1 3-oxo-dodecanoic acid 
• 112-31-2 caprinaldehyde 
• 933486-31-8 C₁₂H₂₄O₂ 
• 67-56-1 methanol 
• 117951-87-8 1-tridecen-4-ol 
• 182359-65-5 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 112-13-0 n-decanoyl chloride 

Downstream Products

• 157459-92-2 (R)-3-((2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-dodecanoic acid 
• 157459-93-3 (R)-3-((2R,3R,4S,5S,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-dodecanoic acid methyl ester 

Relevant academic research and scientific papers

An Improved Asymmetrically-Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel

The ultrasonic irradiation of Raney nickel catalyst in water followed by the removal of the resulting turbid supernatant gave an excellent nickel catalyst (RNi-U) which generated an asymmetrically-modified nickel catalyst.An EPMA (SEM-EDX) study indicated that RNi-U consisted of a fairly pure nickel surface of homogeneous size.Tartaric acid-NaBr-modified RNi-U (TA-NaBr-MRNi-U) showed a high enantio-differentiating ability as well as reactivity in the hydrogenation of prochiral ketones such as 1,3-diones and 3-oxoalkanoic acid esters.

Total synthesis of fellutamide b and deoxy-fellutamides B, C, and D

The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.

Asymmetric synthesis of long chain β-hydroxy fatty acid methyl esters as new elastase inhibitors

Herein, β-hydroxy methyl esters with an even carbon chain length of 12-20 1b-5b were synthesized by three different asymmetric reduction methods I, II III from their corresponding β-keto methyl esters 1a-5a with the aim of determining their elastase activities. In method I, chiral catalyst A was prepared from chiral ligand (R)-binaphthol 1, while in method II, chiral catalyst B was synthesized from (2R,3R)-diisopropyl tartrate 2. Chiral catalyst B has not previously been used in asymmetric borane reductions or in the asymmetric synthesis of chiral β-hydroxy methyl esters. In method III, an asymmetric reduction was catalysed by (R)-Me-CBS oxazaborolidine 3. Hydride transfer was carried out in all of these methods by BH3· SMe2. Chiral hydroxy methyl esters with an (S)-configuration were synthesized by method I and with an (R)-configuration via methods II and III. The chiral hydroxy methyl esters obtained were analysed by chiral HPLC for their ee % values. Methods I, II and III were applied to long chain β-keto methyl esters for the first time. The reduction methods I, II and III were examined in terms of reaction yield and enantiomeric excess according to carbon chain length and the variable ratio of chiral catalysts to β-keto methyl ester. The highest enantiomeric excess of 90% ee was found in method III for 12 and 14 carbon numbers.

Asymmetric synthesis of sphinganine and clavaminol H

(Figure presented) An efficient enantioselective synthesis of sphinganine and clavaminol H is reported. These sphingoid-type bases were obtained from commercially available fatty acids using highly enantioselective Ru-catalyzed hydrogenation and organocatalytic electrophilic amination reactions to create the stereogenic centers.

ESTERS AND AMIDES AS PLA2 INHIBITORS

The present invention relates to a novel fatty acid derivative of formula (I), wherein R1 is acyl group; R2 is acyl(lower)alkyl; R3 is hydrogen, aryl(lower)alkyl, etc.; R4 is acyl(lower)alkyl; and X is —O—, —NH—

Over 98% optical yield achieved by a heterogeneous catalysis. Substrate design and analysis of enantio-differentiating factors of tartaric acid-modified Raney nickel hydrogenation

Tartaric acid-modified Raney nickel (TA-MRNi) is a chiral heterogeneous catalyst for the hydrogenation of prochiral ketones. An optical yield (OY) of 86% with methyl acetoacetate (1) as a substrate was improved to 94-96% by employing β-keto esters having a proper bulkiness at the γ-position. The γ-bulkiness effect contributes to a high intrinsic enantio-differentiating ability (factor-i) of the TA-MRNi catalysis. Through the study, we found the best substrate, γ-cyclopropyl-β-keto ester, the hydrogenation of which resulted in 98.6% OY. This further improvement in the OY was ascribed to a smaller contribution of non-enantio-differentiating hydrogenation (N-site catalysis) due to the substrate-specific activation of the enantio-differentiating hydrogenation by the chiral modifier. The OY of the hydrogenation of 1 was analyzed by comparing with well-behaved β-keto esters, and the contribution of the factor-i and the N-site to the OY value was evaluated to deduce the origin of the enantiodifferentiation.

Total synthesis of arthrobacilin A

Novel cyclic glycolipids, arthrobacilin A and its analogues, have been synthesized by means of unique DCC/DMAP·HCl promoted oligomerization/cyclization, zinc salt catalyzed β-selective glycosylation, and Noyori's BINAP/Ru catalyzed asymmetric reduction.

Highly Efficient Enantio-differentiating Hydrogenation over an Ultrasonicated Raney Nickel Catalyst Modified with Tartaric Acid

A tartaric acid-NaBr-modified nickel catalyst prepared from ultrasonicated Raney nickel showed excellent enantio-differentiating and hydrogenating activity in the hydrogenation of a series of 3-oxoalkanoate and 1,3-diketones.

Asymmetric Reduction of Aliphatic Short- to Long-Chain β-Keto Acids by Use of Fermenting Bakers' Yeast

Eleven β-keto acids, ranging from 3-oxobutanoic to 3-oxooctanoic acids, were reduced with fermenting bakers' yeast to the corresponding optically active β-hydroxy acids, which were isolated as the methyl esters.In all cases, the (R)-hydroxy acids were obtained in >/=98percent ee, except for 3-oxobutanoic acid, which afforded the (S)-hydroxy acid in 86percent ee.Inhibition of fermentation was observed for 3-oxoundecanoic to 3-oxotetradecanoic acids, leading to no reduction.Lowering of the substrate concentration was found to be appreciably effective in avoiding inhibition.

The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII

The enantioface-differentiating hydrogenation of methyl 3-oxoalkanoate (CH3(CH2)nCOCH2COOCH3, n=0, 6, 8, 10, 12) over the (R,R)-tartaric acid-NaBr-modified Raney nickel catalyst ((R,R)-TA-NaBr-MRNi) gave methyl (R)-3-hydroxyalkanoate (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12) in an average optical yield of 85percent.After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (R)-3-hydroxyalkanoic acid (CH3(CH2)nCH(OH)CH2COOH, n=0, 6, 8, 10, 12) in a reasonable yield.From the hydrogenation product with (S,S)-TA-NaBr-MRNi, optically pure (S)-3-hydroxyalkanoic acid was obtained by the same process as above.