142270-14-2Relevant articles and documents
Synthesis of Symmetrical Dodeco-6,7-diuloses
Bayer, Marius,Stocker, Simon,Maichle-M?ssmer, C?cilia,Ziegler, Thomas
, p. 4347 - 4360 (2020)
Dodeco-6,7-diuloses represent a rare class of sugars and can be considered as anomerically linked di-hexoses with two hemiacetal functions in the middle. Herein, the synthesis of three symmetrical dodeco-6,7-diuloses (gluco-gluco, galacto-galacto, manno-manno) is described. For their preparation four synthetic strategies were pursued, whose mutual key step, the connection of the anomeric centers, is particularly emphasized. Specifically, C–C bond forming methods are employed, such as a Grubbs metathesis, a stannyl glycal homocoupling reaction, a coupling of a sulfinyl glycal with a sugar lactone and a Ramberg–B?cklund rearrangement. Since the ring closure via hemiacetal formation of the target compounds cannot be predicted, intensive NMR spectroscopic structure elucidation of the diuloses was performed.
Synthesis and Pd-catalyzed coupling of1-C-stannylated glycals
Bayer, Marius,B?chle, Felix,Ziegler, Thomas
, p. 347 - 369 (2018/09/21)
1-Tributylstannyl glycals were applied as versatile tools in the Pd(0)-mediated synthesis of glycal phthalonitrile conjugates. Likewise, selective homo-coupling of 1-tributylstannyl glycals furnishing C1-C1’ linked glycal dimers was investigated by using Pd(II)-species. For both Stille type couplings the rate-accelerating effect of copper(I) thiophene-2-carboxylate (CuTC) was exploited. The synthesis of stannylated glycal precursors was significantly improved by establishing a one-pot two-step procedure via glycosyl sulfoxides.
Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-D-glucals with organic halides
Dubois, Eric,Beau, Jean-Marie
, p. 103 - 120 (2007/10/02)
1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst.This mild reaction is specially useful for the preparation of 1-C-aryl-
Formation of C-Glycosides by a Palladium-catalysed Coupling Reaction of Tributylstannyl Glycals with Organic Halides
Dubois, Eric,Beau, Jean-Marie
, p. 1191 - 1192 (2007/10/02)
The palladium-catalysed coupling reaction of 1-(tributylstannyl)-D-glucals with unsaturated halides furnishes the corresponding 1-C-alkylated glucals, an efficient procedure for a symmetric or dis-symmetric di-C-glycosidation of 1,3-dibromobenzene.
