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; galactopyranosylacceptors; galactose donors; molecular modeling; regioselectivity; Introduction
Given the importance of
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-galactopyranosylacceptors 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 galactopyranosylacceptors 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
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Graphical Abstract
Figure 1:
Monobenzylated methyl α- and β-D-gluco- and galactopyranoside acceptors 1–6.