Kawabata, Takeo’s team published research in Journal of the American Chemical Society in 129 | CAS: 85618-21-9

Kawabata, Takeo published the artcileA Catalytic One-Step Process for the Chemo- and Regioselective Acylation of Monosaccharides, SDS of cas: 85618-21-9, the publication is Journal of the American Chemical Society (2007), 129(42), 12890-12895, database is CAplus and MEDLINE.

An organo-catalytic method for the chemo- and regioselective acylation of monosaccharides has been developed. Treatment of octyl β-D-glucopyranoside with isobutyric anhydride in the presence of 10 mol % of a C₂-sym. chiral 4-pyrrolidinopyridine catalyst at -50 °C gave the 4-O-isobutyryl derivative as the sole product in 98% yield. Thus, chemoselective acylation, favoring a secondary hydroxyl group in the presence of a free primary hydroxyl group, and regioselective acylation, favoring one of three secondary hydroxyl groups, took place with perfect selectivity. A competitive acylation between octyl β-D-glucopyranoside and a primary alc. (2-phenylethanol) with 1.1 equiv of isobutyric anhydride in the presence of 4-pyrrolidinopyridine catalyst gave the 4-O-isobutyrate of octyl β-D-glucopyranoside with 99% regioselectivity in 98% yield, which indicates that acylation of the secondary hydroxyl group at C(4) of the carbohydrate proceeds in an accelerative manner. A possible mechanism, involving multiple hydrogen-bonding between 4-pyrrolidinopyridine catalyst and the monosaccharide, is proposed for the chemo- and regioselective acylation.

Journal of the American Chemical Society published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, SDS of cas: 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts