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. 2016 Nov 9;8(3):1867–1875. doi: 10.1039/c6sc04638j

Table 1. Model acceptor glycosylations.

Acceptor N a F b graphic file with name c6sc04638j-u1.jpg graphic file with name c6sc04638j-u2.jpg graphic file with name c6sc04638j-u3.jpg
Product, α : β (yield) c Product, α : β (yield) c Product, α : β (yield) c
graphic file with name c6sc04638j-u4.jpg 1A 2A 3A
1 : 6 1 : 5 1 : 8
(96%) (71%) (83%)
graphic file with name c6sc04638j-u5.jpg 7.44 0.01 1B 2B 3B
1 : 5 1 : 10 1 : 8
(70%) (68%) (95%)
graphic file with name c6sc04638j-u6.jpg 0.15 1C 2C 3C
1 : 5 1 : 3 1 : 6
(86%) (70%) (70%)
graphic file with name c6sc04638j-u7.jpg 0.29 1D 2D 3D
1 : 5 5 : 1 1 : 5
(90%) (70%) (87%)
graphic file with name c6sc04638j-u8.jpg 1.11 0.38 1E 2E 3E
1 : 4 >20 : 1 1 : 2.5
(78%) (64%) (85%)
graphic file with name c6sc04638j-u9.jpg –1.93 1F 2F 3F
3 : 1 >20 : 1 1 : 1
(56%) (65%) (52%)
graphic file with name c6sc04638j-u10.jpg 3.58 1G 2G 3G
<1 : 20 >20 : 1 <1 : 20
(60%) (79%) (95%)
graphic file with name c6sc04638j-u11.jpg 1.68 1H 2H 3H
<1 : 20 >20 : 1 <1 : 20
(44%) d (42%) d (40%) d

aMayr's nucleophilicity parameters.

bField inductive parameters.

cα/β-Ratios were established by NMR spectroscopy of the crude and purified reaction mixtures.

dBoth anomers of donor glycoside were also found after the glycosylation reaction. Literature yields of 1H 40: 57% and 2H 40: 56%.