Carbohydrate chiral-pool approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates

Abstract

D-Glucose, L-xylose, and D-and L-arabinose were sources of chirality to obtain four enantiomerically pure 3-hydroxy-2-methylbutanoic acids, which were reacted with 2-naphthyldiazomethane to furnish their fluorescent 2-naphthylmethyl esters.

Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: Role of the length of alditol side chain

“…The primary hydroxyl of 6 was selectively protected with an acetyl (Ac) moiety to give 1-O-acetyl-2,4-O-benzylidene-D-erythritol (7) in 89% yield. Subsequent regioselective reductive-cleavage of benzylidene acetal 7 was achieved by treatment with triethylsilane in the presence of BF 3 ÁEt 2 O to give 1-O-acetyl-4-O-benzyl-D-erythritol (8), which was acetalized with 2,2-dimethoxypropane (DMP) to give 1-O-acetyl-4-O-benzyl-2,3-O-isopropylidene-D-erythritol (9). The deacetylation of 9 and subsequent silylation of the resulting monoalcohol, 4-O-benzyl-2,3-O-isopropylidene-D-erythritol (10), gave 4-O-benzyl-1-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-erythritol (11).…”

3-Deoxy-1,2-di-O-isopropylidene-5-O-tosyl-D-threo-pentofuranose

“…Title compound was obtained as a product of a multi-step synthetic procedure (Doboszewski & Herdewijn, 2008; see Fig. 1).…”

“…For the syntheses of this and similar compounds, see: Cox et al (1997); Dahlman et al (1986); Doboszewski & Herdewijn (1996, 2008. For conformations of five-membered rings, see: Cremer & Pople (1975); Boeyens & Dobson (1987).…”

“…commercially available, reasonably priced, and easy to functionalize in two steps to form 5-O-t-butyldiphenylsilyl-1,2-Oisopropylidene furanose or its L-enantiomer (Dahlman et al, 1986;Doboszewski & Herdewijn, 2008). Both enantiomers have been previously used in the synthesis of degradation products of the antibiotic Batumin/Kalimantacin A (Doboszewski & Herdewijn, 2008), to obtain branched-chain pyranosyl nucleosides (Doboszewski & Herdewijn, 1996) and C-hydroxymethylpentose present in lipopolysaccharides of Coxiella brunetii (Dahlman et al, 1986), among others.…”

“…Both enantiomers have been previously used in the synthesis of degradation products of the antibiotic Batumin/Kalimantacin A (Doboszewski & Herdewijn, 2008), to obtain branched-chain pyranosyl nucleosides (Doboszewski & Herdewijn, 1996) and C-hydroxymethylpentose present in lipopolysaccharides of Coxiella brunetii (Dahlman et al, 1986), among others.…”