Our recent study showed that 4,6-di-O-benzylidenyl group, coupled with 3-O-t-butyldiphenylsilyl (TBDPS) protection group, could direct the preparation of 2-deoxy-2-azido-α-D-galactopyranoside from 2-deoxy-2-azido-1-thio-D-galactopyranoside. It was proposed that the lone pairs on 4,6-di-O-benzylidenyl group could influence the stereoselectivity of the reaction. In this study, we will employ density functional theory (DFT) to explore the steric, geometric, and electronic factors of 4,6-di-O-benzylidenyl group and 3-O-t-butyldiphenylsilyl protection group on the selectivity. In addition to the crystal structure, a total of eighteen (18) 2-deoxy-2-azido-1-thio-D-galactopyranoside conformations will be examined. The electronic density of these conformations will be investigated to reveal the geometric and steric influence on the electronic density of 2-deoxy-2-azido-1-thio-D-galactopyranosides. The study will shed lights on the source of the selective synthesis of 2-deoxy-2-azido-α-D-galactopyranosides.

Steric, geometric, and electronic influence of by 3-O-TBDPS and 4,6-di-O-Benzylidenyl group on the selective synthesis of 2-deoxy-2-azido-α-D-galactopyranosides

ACS Spring 2022

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