Chiral crown ethers incorporating D-glucose

Abstract

A novel class of crown ether derivatives incorporating D-glucose and poly(ethy1ene glycol) units has been synthesized from allyl a-D-glucopyranoside by a simple and efficient strategy. The complexing properties of these compounds with alkali metal cations and ammonium ion have been evaluated by Cram's picrate method. Catalytic activity of macrocycle 2 in asymmetric Michael addition reaction was also studied. The average cavity size of these macrocycles was determined by the application of the MMX programme.

Linkage position and residue identification of disaccharides by tandem mass spectrometry and linear discriminant analysis

“…1,4-Linked disaccharide DS249 (Man-Glc-propyl) started with the known acceptor allyl 2,3,6-tri-O-benzyl-a-D-glucopyranoside, which can be prepared from D-glucose in four steps. 40 Glycosylation of this acceptor with donor (5) provides a disaccharide with protecting groups. The final 1,4-linked disaccharide DS249 can be obtained after deacetylation and catalytic hydrogenation.…”

“…The deprotected propyl‐glycosides DS232 and DS247 can be obtained after coupling the above intermediate disaccharides with n‐propanol (to give the corresponding propyl‐glycosides) and deacetylation. 1,4‐Linked disaccharide DS249 (Man‐Glc‐propyl) started with the known acceptor allyl 2,3,6‐tri‐ O ‐benzyl‐ α‐D‐glucopyranoside, which can be prepared from D‐glucose in four steps 40. Glycosylation of this acceptor with donor (5) provides a disaccharide with protecting groups.…”

Sugar Derived Crown Ethers and Their Analogs: Synthesis and Properties

“…Asymmetric induction in the Michael addition of methyl phenylacetate to methyl acrylate in the presence of these receptors was studied, however, no concise results were obtained [40].…”

“…* First synthesis of such receptors from allyl -D-glucopyranoside was proposed by Mani and Nair [39,40]. Protection of the free hydroxyl groups followed by reductive opening of the benzylidene acetal [41] and allylation of the resulting alcohol provided allyl 4-O-allyl-2,3,6-tri-O-benzyl--D-glucopyranoside (5 6 ).…”

The Synthesis of Hydrobenzoin-Based Monoaza Crown Ethers and Their Application as Recyclable Enantioselective Catalysts

“…Chiral crown ethers have also been used in enantioselective syntheses as phase transfer catalysts [19]. Macrocycles derived from binaphtol, [20,21] carbohydrates, [22][23][24][25][26] spirobiindane [27] and other chiral diols [28][29][30][31] have all been used efficiently in different asymmetric reactions. In our group, monoaza-15-crown-5-type lariat ethers incorporating a carbohydrate unit were synthesized [32,33].…”