Topic
Glucal
About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.
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TL;DR: In this paper, Naphthyl 3,4,6-tri tri -O-methyl-β-d -glucopyranoside was applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate.
Abstract: Naphthyl 3,4,6- tri -O- methyl-β- d -glucopyranoside , easily synthesized from tri -O- acetyl- d -glucal , has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high facial diastereoselection (>95%) was obtained. No diastereoselection was observed when 1,3,4,6- tetra -O- methyl-β- d -glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account steric shielding and π-stacking effects, is proposed on the basis of the observed results.
14 citations
TL;DR: In this paper, the authors proposed a method to give the dimethyl acetal of 2-C-formyl-Dalditol derivatives using the catalytic system [Rh(µ-OMe)(cod)]2/P(O-o-ButC6H4)3/PPTS is strongly dependent on the protecting groups on the carbohydrate.
14 citations
TL;DR: Synthese d'anhydro-3,6 O-t-butyldimethylsilyl-4 glucal a partir d'O-tosyl-6 glucal et de butyl chloro dimethyl silane
14 citations
TL;DR: In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
Abstract: N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereoselective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived from tri-O-acetyl-D-glucal.
14 citations
TL;DR: Molybdenum catalysts are efficient and selective catalysts for the tandem epoxidation/alcoholysis or epoxide/hydrolysis of glucal and galactal derivatives as mentioned in this paper.
Abstract: Molybdenum catalysts are efficient and selective catalysts for the tandem epoxidation/alcoholysis or epoxidation/hydrolysis of glucal and galactal derivatives. In glucal derivatives the selectivity is mainly controlled by the allylic substituent at position 3 of the glycal, obtaining in general the products derived from the initial formation of the α-epoxide (gluco) when this hydroxy group is protected, while products derived from the β-epoxide (manno) are mainly obtained when it is unprotected. In galactal derivatives the estereoselectivity is always high to give the α-epoxide (galacto) and independent of the protecting groups.
14 citations