10430-97-4Relevant articles and documents
Racemic and optically active 2-methoxy-4-oxatetradecanoic acids: Novel synthetic fatty acids with selective antifungal properties
Carballeira, Nestor M.,O'Neill, Rosann,Parang, Keykavous
, p. 47 - 54 (2005)
The unprecedented (±)-2-methoxy-4-oxatetradecanoic acid and the optically pure (S)-2-methoxy-4-oxatetradecanoic acid were synthesized in six steps and in 11-14% overall yields starting with either 1,2-O-isopropylidene- rac-glycerol or 1,2-O-isopropylidene-(S)-glycerol. The key step in the synthesis was the selective monosilylation of a dibutylstannylene intermediate. The title compounds displayed selective fungitoxicity in the range of 0.08-0.22 mM against Cryptococcus neoformans ATCC 66031 and Aspergillus niger ATCC 16404, but no significant activity against C. albicans ATCC 14053 and ATCC 60193 (>2.6 mM). Albeit being good substrates for N-myristoyltransferases (NMTs), the racemic and the S-enantiomer of the oxygenated 2-methoxylated compounds showed no significant difference in antifungal activity. This finding suggests an alternative mechanism of fungitoxicity other than NMT inhibition.
A novel regioselective desulfation method specific to silyl ester of primary sulfate using silylating agents. Selective preparation of secondary alkyl sulfates having a primary hydroxy group
Horibe,Oshita
, p. 181 - 182 (2001)
The treatment of bis(trimethylsilyl)ester of 1-O-Decylglycerol-2,3-Disulfate with trimethylsilyl-N-trimethylsilylacetimidate (BSA) or (dimethylamino)trimethylsilane caused regioselective desulfation to afford 1-O-decyl glycerol-2-sulfate selectively in good yield. Silylating agents, having nitrogen, seems to be responsible for facilitating trimethylsiloxysulfonyl cation transfer.
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Eremenko,L.T.,Korolev,A.M.
, (1977)
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METHOD FOR PREPARING GLYCEROL ETHER AND GLYCOL ETHER
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Paragraph 0072, (2015/03/28)
The present invention concerns a method for preparing glycerol ether or glycol ether comprising the reaction of a compound of formula (II) with a compound of formula (III) in the presence of a heterogeneous acid catalyst of formulas (II) and (III).
1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction
Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
, p. 786 - 797 (2013/04/24)
From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.