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• W2146751423 endingPage "3787" @default.
• W2146751423 startingPage "3787" @default.
• W2146751423 abstract "A trifluoroacetate-catalyzed opening of the oxirane ring of glycidyl derivatives bearing allylic acyl or alkyl functionalities with trifluoroacetic anhydride (TFAA), provides an efficient entry to configurationally homogeneous 1(3)-acyl- or 1(3)-O-alkyl-sn-glycerols. Selective introduction of tert-butyldimethylsilyl- (TBDMS), or triisopropylsilyl- (TIPS) transient protections at the terminal sites within these key intermediates secures 1(3)-acyl- or 1(3)-O-alkyl-3(1)-O-TBDMS (or TIPS)-sn-glycerols as general bifunctional precursors to 1,2(2,3)-diacyl-, 1(3)-O-alkyl-2-acyl- and 1,3-diacyl-sn-glycerols and hence triester isosters. Incorporation of a requisite acyl residue at the central carbon of the silylated synthons with a subsequent Et3N·3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment at the stereogenic C2-centre of the monosilylated glycerides; (ii) replacement of the silyl moiety by a short- or long-chain carboxylic acid residue by means of the acylating agent: tetra-n-butylammonium bromide (TBABr)–carboxylic acid anhydride (CAA)–trimethylsilyl bromide (TMSBr); and (iii) removal of the trichloroacetyl replacement, provides pure 1,3-diacyl-sn-glycerols. The TBABr–CAA–TMSBr reagent system allows also a one-step conversion of 1,2-diacylglycerol silyl ethers into homochiral triglycerides with predefined asymmetry and degree of unsaturation. These compounds can also be accessed via a two-step one-pot approach where the trichloroacetyl derivatives of 1,2(2,3)- or 1,3-diacyl-sn-glycerols serve as triester building blocks for establishing the third ester bond at preselected C3(1)- or C2-positions within the glycerol skeleton at the very last synthetic stage. In all instances, the target compounds were produced under mild conditions, in high enantiomeric purity, and in practically quantitative yields." @default.
• W2146751423 created "2016-06-24" @default.
• W2146751423 creator A5057347366 @default.
• W2146751423 creator A5085989985 @default.
• W2146751423 date "2007-01-01" @default.
• W2146751423 modified "2023-10-13" @default.
• W2146751423 title "Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides" @default.
• W2146751423 cites W1895065514 @default.
• W2146751423 cites W1963892755 @default.
• W2146751423 cites W1965795276 @default.
• W2146751423 cites W1966370803 @default.
• W2146751423 cites W1966708424 @default.
• W2146751423 cites W1971222985 @default.
• W2146751423 cites W1971720953 @default.
• W2146751423 cites W1976243466 @default.
• W2146751423 cites W1976700494 @default.
• W2146751423 cites W1978468660 @default.
• W2146751423 cites W1978794147 @default.
• W2146751423 cites W1979699051 @default.
• W2146751423 cites W1981143349 @default.
• W2146751423 cites W1981738513 @default.
• W2146751423 cites W1984479895 @default.
• W2146751423 cites W1984484237 @default.
• W2146751423 cites W1985373204 @default.
• W2146751423 cites W1985407738 @default.
• W2146751423 cites W1986573185 @default.
• W2146751423 cites W1988432891 @default.
• W2146751423 cites W1992773933 @default.
• W2146751423 cites W1992868668 @default.
• W2146751423 cites W1994079051 @default.
• W2146751423 cites W1997566679 @default.
• W2146751423 cites W2007708678 @default.
• W2146751423 cites W2008272325 @default.
• W2146751423 cites W2010455307 @default.
• W2146751423 cites W2010500991 @default.
• W2146751423 cites W2011755656 @default.
• W2146751423 cites W2013227503 @default.
• W2146751423 cites W2014295190 @default.
• W2146751423 cites W2016834421 @default.
• W2146751423 cites W2016960960 @default.
• W2146751423 cites W2017577519 @default.
• W2146751423 cites W2018025503 @default.
• W2146751423 cites W2018637245 @default.
• W2146751423 cites W2019468990 @default.
• W2146751423 cites W2023653753 @default.
• W2146751423 cites W2023989785 @default.
• W2146751423 cites W2025127136 @default.
• W2146751423 cites W2026659705 @default.
• W2146751423 cites W2028044676 @default.
• W2146751423 cites W2029135107 @default.
• W2146751423 cites W2030725409 @default.
• W2146751423 cites W2030747921 @default.
• W2146751423 cites W2031049343 @default.
• W2146751423 cites W2031903330 @default.
• W2146751423 cites W2032079586 @default.
• W2146751423 cites W2032640520 @default.
• W2146751423 cites W2033301315 @default.
• W2146751423 cites W2034604113 @default.
• W2146751423 cites W2036390127 @default.
• W2146751423 cites W2039295798 @default.
• W2146751423 cites W2039405168 @default.
• W2146751423 cites W2039513549 @default.
• W2146751423 cites W2039673672 @default.
• W2146751423 cites W2040268493 @default.
• W2146751423 cites W2041200468 @default.
• W2146751423 cites W2042876400 @default.
• W2146751423 cites W2042970955 @default.
• W2146751423 cites W2043741485 @default.
• W2146751423 cites W2045511459 @default.
• W2146751423 cites W2046963620 @default.
• W2146751423 cites W2047309725 @default.
• W2146751423 cites W2047618403 @default.
• W2146751423 cites W2047630385 @default.
• W2146751423 cites W2051753918 @default.
• W2146751423 cites W2052130504 @default.
• W2146751423 cites W2052316288 @default.
• W2146751423 cites W2057744727 @default.
• W2146751423 cites W2060034770 @default.
• W2146751423 cites W2060593186 @default.
• W2146751423 cites W2060779029 @default.
• W2146751423 cites W2061145896 @default.
• W2146751423 cites W2063472067 @default.
• W2146751423 cites W2064104709 @default.
• W2146751423 cites W2067326418 @default.
• W2146751423 cites W2070930715 @default.
• W2146751423 cites W2071801044 @default.
• W2146751423 cites W2072905811 @default.
• W2146751423 cites W2074678219 @default.
• W2146751423 cites W2075184689 @default.
• W2146751423 cites W2075262061 @default.
• W2146751423 cites W2077040986 @default.
• W2146751423 cites W2078243141 @default.
• W2146751423 cites W2080497758 @default.
• W2146751423 cites W2081868653 @default.
• W2146751423 cites W2084036644 @default.
• W2146751423 cites W2085800204 @default.
• W2146751423 cites W2086644725 @default.
• W2146751423 cites W2092121399 @default.

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