New route to enantiomers of cyclic β-hydroxyethers. The crystal structure of (S)-(+)-tetrahydrofurfuryl-O,O′-diacetyl-(2R,3R)-hydrogentartrate

Mravik, András; Böcskei, Zsolt; Keszei, S.; Elekes, Ferenc; Fogassy, Elemér

doi:10.1016/0957-4166(96)00165-6

Cited by 9 publications

(6 citation statements)

References 27 publications

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“…1) consists of the hydrogentartrate fragment in which the carboxyl group and the lactone ester group are in anti conformation with the torsion angle C1-C2-C3-C4 equal to 172.8 (2)°. The same conformation is observed in (S)-tetrahydrofurfuryl -O,O′-diacetyl-(R,R)-hydrogentartrate (Mravik et al, 1996) were the relevant torsion angle is 168.1 (5)°. Whereas in the second structurally characterized derivative, (S)-timolol-O,O′-diacetyl-(R,R)hydrogentartrate (Kivikoski et al, 1993) the gauche conformation is observed and the corresponding torsion angle equals to 37.0 (5)°.…”

Section: Data Collectionsupporting

confidence: 63%

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TheO,O′-diacetyl (R,R)-hydrogentartrate ester of (S)-pantolactone

et al. 2007

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The synthesis of the title compound, (1R,2R)‐1‐carboxy‐2‐[(3S)‐4,4‐dimethyl‐2‐oxotetrahydrofuran‐3‐yloxycarbonyl]ethane‐1,2‐diyl diacetate, C14H18O10, from diacetyltartaric acid anhydride and pantolactone gave two enantiomeric pairs and the crystal structure of the R,R,S enantiomer is presented here. The molecule consists of a hydrogen tartrate fragment in which the carboxyl group and the lactone ester group are in an anti conformation. In the crystal structure, molecules are linked into C(10) chains by an intermolecular O—H...O hydrogen bond and further by C—H...O interactions to form a layer structure with the second‐level graph‐set descriptor R22(8)[R44(26)].

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Section: Data Collectionsupporting

confidence: 63%

“…The molecular geometry is close to that of the (R,R,S) isomer but the molecules are O-HÁ Á ÁO linked via water molecules to form a layer structure. There are only two other structurally characterized (R,R)-hydrogentartrate esters to date (Kivikoski et al, 1993;Mravik et al, 1996).…”

Section: Related Literaturementioning

confidence: 99%

TheO,O′-diacetyl (R,R)-hydrogentartrate ester of (S)-pantolactone

et al. 2007

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“…The corresponding R,R,S diastereoisomer forms anhydrous crystals (Zachara et al, 2007). There are only two other structurally characterized (R,R)-hydrogentartrate esters to date (Kivikoski et al, 1993;Mravik et al, 1996). For related literature, see: Allen et al (1998).…”

Section: Related Literaturementioning

confidence: 99%

TheO,O′-diacetyl (R,R)-hydrogentartrate ester of (R)-pantolactone monohydrate

Zachara¹,

Madura²,

Bernaś³

et al. 2007

Acta Cryst E

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“…Diacetyltartaric acid anhydride, (I), is an important intermediate in the synthesis of anionic oil-in-water emulsifiers, such as the diacetyltartaric esters of monoglycerides (DATEMs), which are used throughout the world as improvers in bread-making (Kö hler & Grosch, 1999). This compound has also been used in studies of the kinetic acylation of various racemic alcohols and amines, a process that sometimes helps to separate racemates into their pure enantiomeric components (Mravik et al, 1996). Compound (I) was prepared by the reaction of tartaric acid and acetic anhydride (Ireland & Thompson, 1979).…”

Section: Commentmentioning

confidence: 99%