Regioselectivity of glycosylation reactions of galactose acceptors: an experimental and theoretical study

• Enrique A. Del Vigo,
• Carlos A. Stortz and
• Carla Marino

Beilstein J. Org. Chem. 2019, 15, 2982–2989, doi:10.3762/bjoc.15.294

• some of the acceptors. However, the Galp-(β1→3)-Galp linkage could be regioselectively installed by using some of the acceptors assayed herein. Keywords: Fukui indexes; galactopyranosyl acceptors; galactose donors; molecular modeling; regioselectivity; Introduction Given the importance of

Acceptor-influenced and donor-tuned base-promoted glycosylation

• Stephan Boettcher,
• Martin Matwiejuk and
• Joachim Thiem

Beilstein J. Org. Chem. 2012, 8, 413–420, doi:10.3762/bjoc.8.46

• yields of up to 95%. Preparation of the 3-O-monobenzylated methyl α- and β-D-galactopyranosyl acceptors 5 and 6 was achieved via stannylidene acetals [6] (Scheme 2). Compound 18 was subjected to a one-step synthesis with Bu2SnO and BnBr, affording target compound 5. The synthetic route for the methyl β

• , reflux. Synthesis of 3-O-monobenzylated gluco- und galactopyranosyl acceptors 5 and 6. Reagents and conditions: (a) Benzaldehyde dimethylacetal, camphorsulfonic acid, ACN, 80 °C, 2.5 h; (b) dibutyltin oxide, toluene, BnBr, 24 h, reflux; (c) MeOH, H2O, HCl, 2–22 h, reflux. Synthesis of 2,3,4,6-tetra-O