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. Author manuscript; available in PMC: 2021 Aug 12.
Published in final edited form as: Chem Rev. 2020 Jul 5;120(15):7104–7151. doi: 10.1021/acs.chemrev.0c00243

Table 12.

Influence of Esters at the Galactopyranoside 4-Position on Anomeric Selectivity

graphic file with name nihms-1606546-t0088.jpg
R % yield α:β ratio σp258 F258 gg/gt/tg
H 68 1.7/1 0 0 21.9/34.4/43.7
Me 90 2.9/1 −0.17 0.01 -
CH2Ph 91 2.2/1 −0.09 −0.04 13.2/22/6/64.2
CH2CF3 58 2.3/1 0.09 0.15 11.7/21.7/66.7
COMe 76 7.2/1 0.50 0.33 16.4/31.0/52.6
COCMe3 74 16/1 0.32 0.26 15.0/28.6/56.4
COCCl3 72 4.5/1 - - 6.9/18.8/74.3
COCF3 71 3.0/1 0.46 0.58 7.7/19.2/73.0
COPh 72 17/1 0.43 0.31 15.6/30.5/53.9
COC6H4-4-Me 82 18/1 - - 15.4/32.0/52.5
COC6H4-4-OMe 85 33/1 - - 16.2/32.5/51.3
COC6H4-4-NO2 87 14/1 - - 17.3/23.5/59.1