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. Author manuscript; available in PMC: 2010 Jan 1.
Published in final edited form as: Org Lett. 2009 Jan 1;11(1):9–12. doi: 10.1021/ol8022006

Table 3.

Lactol and Electrophile Scopea

graphic file with name nihms-86656-t0016.jpg
Entry LACTOL electrophile 2-deoxy-β-glycoside yieldb (β:α)c
1 13 graphic file with name nihms-86656-t0017.jpg graphic file with name nihms-86656-t0018.jpg 70% (20:1)
2 13 graphic file with name nihms-86656-t0019.jpg graphic file with name nihms-86656-t0020.jpg 85% (8:1)
3 13 graphic file with name nihms-86656-t0021.jpg graphic file with name nihms-86656-t0022.jpg 75% (20:1)
4 14 graphic file with name nihms-86656-t0023.jpg graphic file with name nihms-86656-t0024.jpg 90% (16:1)
5 14 graphic file with name nihms-86656-t0025.jpg graphic file with name nihms-86656-t0026.jpg 80% (20:1)
6 13 graphic file with name nihms-86656-t0027.jpg graphic file with name nihms-86656-t0028.jpg 61% (20:1)
7 13 graphic file with name nihms-86656-t0029.jpg graphic file with name nihms-86656-t0030.jpg 77% (20:1)
a

Reactions performed at 0.1 M.

b

Isolated yield after chromatographic purification.

c

As determined by 1H NMR (600 MHz)