40653-17-6Relevant articles and documents
General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses
Mulani, Shaheen K.,Cheng, Kuang-Chun,Mong, Kwok-Kong T.
, p. 5536 - 5539 (2015/12/01)
A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.
Stereoselective Synthesis of the C27-C48 Moiety of Aflastatin A by a Carbohydrate Strategy Using a Tin(II)-Mediated Aldol Reaction
Murakoshi, Sawato,Hosokawa, Seijiro
, p. 2437 - 2441 (2015/10/19)
The C27-C48 segment of aflastatin A was synthesized by using d-mannoside and l-erythrulose derivatives as chiral building blocks. The aldol reaction of undecan-2-one with mannolactone and a subsequent reduction gave the C37 and C39 stereogenic centers wit
Application of the anomeric samarium route for the convergent synthesis of the C-linked trisaccharide α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man and the disaccharides α-D-Man-(1→3)-D-Man and α-D-Man-(1→6)-D-Man
Mikkelsen, Lise Munch,Krintel, Sussie Lerche,Jimenez-Barbero, Jesus,Skrydstrup, Troels
, p. 6297 - 6308 (2007/10/03)
Studies are reported on the assembly of the branched C-trisaccharide, α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides α-D-Man-(1→3)-D-Man and α-D-Man-(1→6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.
A flexible route to mannose 6-phosphonate functionalized derivatives
Vidal, Sebastien,Montero, Jean-Louis,Leydet, Alain,Morere, Alain
, p. 2363 - 2377 (2007/10/03)
A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl α-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.
Synthesis of 1,2-trans C-glycosyl compounds by reductive samariation of glycosyl iodides
Miquel,Doisneau,Beau
, p. 2347 - 2348 (2007/10/03)
Reductive samariation of per-O-trimethylsilyl or benzyl glycopyranosyl iodides in the presence of carbonyl compounds provides the corresponding 1,2-trans-C-glycosyl compounds in good yields.
