220984-79-2Relevant academic research and scientific papers
Synthesis of benzyl tetra-O-acetyl-α-L-glucopyranoside from benzyl 2,3-dideoxy-β-D-Erythro-hex-2-enopyranoside
Okazaki, Hayato,Ueda, Yuji,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
, p. 862 - 871 (2017)
Benzyl tetra-O-acetyl-α-L-glucopyranoside was synthesized from benzyl 2,3-dideoxy-β-D-erythro-hex-2-enopyranoside in six steps and 19% overall yield. Epoxidation from the β-side of the double bond between C-2 and C-3 of the starting material along with the subsequent regioselective ring opening by the backside attack of a hydroxide ion at C-3 furnished an intermediate with D-ido-stereochemistry. The inversion at C-5 was performed by an epimerization, by way of an N-cyclohexylenamine, after the chemoselective oxidation at primary hydroxy group of the C-6 to an aldehyde. The present synthesis of L-glucose derivatives implies the sequential stereochemical inversion of C-2 to C-5 of D-glucose. As the present synthesis keeps the whole skeleton and the order of carbon atoms based on the original numbering of D-glucose, it would work well for the synthesis of specifically labeled derivatives, beginning from isotopically labeled D-glucoses.
On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2
Danieli, Bruno,Peri, Francesco,Roda, Gabriella,Carrea, Giacomo,Riva, Sergio
, p. 2045 - 2060 (2007/10/03)
Subtilisin-catalyzed esterification of several enatiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated.
