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. Author manuscript; available in PMC: 2021 May 1.
Published in final edited form as: Org Lett. 2020 Apr 13;22(9):3649–3654. doi: 10.1021/acs.orglett.0c01153

Table 3.

Tetrasaccharide Optimization

graphic file with name nihms-1589234-t0004.jpg
entryd activation method scavenger temp yield (α-only)a
1 preactivation TTBP −10 °C 28%
2 coactivation TTBP −10 °C trace
3b preactivation TTBP −30 °C → −10 °C 31%
4c preactivation TTBP −10 °C 30%
5 preactivation IBO −10 °C trace
6 preactivation β-Pinene −10 °C trace
a

Isolated yield.

b

4 added at −30 °C.

c

rxn time 23 h,

d

1:3 donor/acceptor ratio for all reactions.