61549-47-1Relevant academic research and scientific papers
FMOC PROTECTED (2S)-2-AMINO-8-[(1,1-DIMETHYLETHOXY)AMINO]-8-OXO-OCTANOIC ACID, (S)-2-AMINO-8-OXONONANOIC ACID AND (S)-2-AMINO-8-OXODECANOIC ACID FOR PEPTIDE SYNTHESIS
-
Page/Page column 37, (2019/12/04)
The invention discloses Fmoc protected (2S)-2-amino-8-[(1,1- dimethylethoxy)amino]-8-oxo-octanoic acid, (S)-2-amino-8- oxononanoic acid and (S)-2-amino-8-oxodecanoic acid for use in peptide synthesis, such as solid phase synthesis, as well as the peptide H3K27 (Ac-Lys-Ala-Ala-Arg-Aox-Ser-Ala-NH2) prepared from Fmoc protected (2S)-2-amino-8-[(1,1-dimethylethoxy)amino]-8-oxo-octanoic acid (Aox). These three exemplary compounds as well as their unprotected forms are claimed in the form of four generic formulae. The first of these four formulae is (formula (I)) where -NPro is a protected amino group, such as an amino group protected with a base-labile protecting group, -L- is alkylene, heteroalkylene, arylene or aralkylene, -X- is a covalent bond, -N(H) - or -N(RN)-, where -RN is alkyl, -R2 is hydrogen or alkyl, -R3 is alkyl, such as C2-10 alkyl, or heterocyclyl, and -LAA- and -R1 are as defined in the claims.
Olefin-Methathese. XXII. Metathese von carbonyl-geschuetztem Allylaceton mit Monoolefinen an zinnalkylaktiviertem Re2O7/Al2O3
Warwel, Siegfried,Puetz, Gabriele
, p. 323 - 330 (2007/10/02)
Olefin metathesis of allylacetone usually proceeds with little conversion.After the carbonyl group is protected by (i) silylation with ClSi(CH3)3 to give silylenolethers or (ii) by acetalisation with 1,2-ethanediol to the 1,3-dioxane derivative the reactivity increases significantly in the homometathesis reaction as well as in the co-metathesis with mono-olefins.Using Re2O7/Al2O3 + Sn(CH3)4 as catalyst the metathesis of allylacetone as its silylenolether or as 1,3-dioxolane proceeds with conversions of 46-53percent while the reaction of unprotected ketone only leads to a conversion of 14percent.Co-metathesis with the double-molar amount of symmetrical internal olefins (4-octene, 5-decene, 7-tetradecene, 9-octadecene) 75-90percent of the protected ketone is converted to give mainly the chain-prolonged silylenolethers or the 1,3-dioxolanes.Allylacetone silylated on a preparative scale was subjected to co-metathesis with 4-octene using MoO3-Re2O7/Al2O3 + Sn(CH3)4 as catalyst.After elimination of the protecting group the perfume substance 5-nonene-2-one was obtained in 61percent yield.
