Degradations and Rearrangement Reactions
2.7
413
⊡ Scheme 62
⊡ Scheme 63
Even on mild C-glycosylation using the TMSCN/TMSOTf system, a notable amount of the
D-psicofuranose derivative 319 degrades to the furan 321 [245]. On reaction with Ph 2 Hg,
the chloride 322 gives the furan 323 exclusively [246]. The bromohydrin 324 degrades into
furan 325 on heating with a base [247] ( > Scheme 64).