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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 1.

Optimization of Disaccharide 15

graphic file with name nihms-1589234-t0002.jpg
entry donor/acceptor scavenger temp yield (α-only)
1a 2:1 TTBP rt 14%b
2a 2:1 TTBP 0 °C 44%b
3a 2:1 DTBMP 0 °C 11%b
4c 2:1 TTBP 0 °C 18%b
5d 1:2 TTBP 0 °C 47%b
6d 1:3 TTBP 0 °C 64%b
7d 1:3 TTBP −10 °C 74%e
8d,f 1:3 TTBP −10 °C 69%e
a

TCE/CH2Cl2 (2.7:1).

b

NMR yield, product identified in a complex with α,α-trehalose.

c

TCE/CH2Cl2/THF (6.5:1:3.2).

d

TCE/CH2Cl2 (1.6:1).

e

Isolated yield.

f

300 mg scale of 8.