Abstract
In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially available benzyl (S)-lactate in 76%, 94% ee (2 steps). Deprotection of the acetyl group using N,N-dimethylethylenediamine afforded benzyl (R)-2-sulfanylpropanoate in 93% yield with 90% ee. These two sulfur-containing benzyl esters were sufficiently odorless to be purified by column chromatography. Direct HPLC analysis was applied to determine the enantiomeric excess without thiazolidin-4-one derivatizations. A complementary debenzylation of benzyl (R)-2-(acetylthio)propanoate was also performed using HBr/AcOH to afford (R)-2-(acetylthio)propanoic acid without critical racemization in 92% yield with 92% ee.
Highlights
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Summary
Molbank 2018, 2018, M9xx; doi: Molbank 2018, 2018, M1010; doi:10.3390/M1010 Representative natural products and biologically active agents/compounds installing the chiral thioMl oslebagnRmk e2e0pn1r8te,ss2e0(Rn18t),a-Mtai9vnxedx n(aSt)u-1raalrperloisdtuedctsinanodurbrieocloegnitcraellpyoarcttaivloenaggwenittsh/ctohme pdoisupnldays ionfstthaleliirngsttrhuectcu2hroierfsa7l[3]. Anti[ap3n]l.atitTpeilloaeptteraloecnttiiavncat[ti4ivn,5ag]tifnaangcdtfoatrcht(ioaornlat(cia-tnPotAmi-FPy)AcaiFnn)t[aa6gn–o9ta]ngiaosrtnesis[let1sa0d,[11i1n0],g1; 1InM]a; tPIuM-r1aP,l-a1a,mnateibtmaiolelttoiac-lβlco-o-lmβac-pltaaocmutanamdsesasi(enFhiignibuhiriteboir2to)[.r12]; vasOo[1pt2he]ep;rvtbiadisoaolspoegepiicntaihdlliaybsiaetcotirinsvhe[i1ba3igt]eo;nrmstse/[ct1ho3im]o; pnmoineutenhdaiomsnaiirnneeodpaeemspcirtniidboepadseepisnti(dcMharseoetnsAo(PlMosg)eitacAcoPtrisdv)eerascoittfievthepersioritbdeeespvre[o1lob4p]e;sms[pe1ne4tc]:;ific subassnptrteiapctilefaisctefslouertbSsattcrrtaeivtpeatstoifnmogrySfcatercestpoRrto6(m1anyDtci,-eDPs-ApRFe6)p1 taDind,Dtaa-sgpeoespn[it1sidt5sa];s[1eas0n,[1d115a]];;nIaMonndPs-at1e,nraoonimdstaeeltrafolaildorn-aβel-sflaoarcindtaemXsoairdseecXeinprehtcoiebrpi(ttoForXr R) ago[(n1F2iXs]t;Rv[)1aa6sg]o.opneipstti[d1a6s]e. Inhibitors [13]; methionine aminopeptidases (MetAPs) active site probes [14]; specific substrates for Streptomyces R61 D,D-peptidases [15]; and a nonsteroidal farnesoid X receptor (FXR) agonist [16].
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