O-Glycosyl Donors
3.4
589
2.8 n-Pentenyl Furanoside Donors
2.8.1 Chemoselective Deprotection of the Anomeric Center
Unlike n-pentenyl pyranosides, the corresponding furanosides have attracted comparatively
little attention. Sharma and Rao reported the preparation of n-pentenyl D-allo-, and D-gulofuranosides 143 and 146, respectively ( > Scheme 19) [55]. They made use of an efficient acidinduced rearrangement of diacetonides 142 and 145, in the presence of n-pentenyl alcohol. The
ensuing pent-4-enyl diacetonides 143 and 146, were chemoselectively cleaved to hemiacetals
144 and 147.
⊡ Scheme 19
Pent-4-enyl furanosides from D-allose and D-gulose diacetonides
⊡ Scheme 20
Pentenyl ribofuranosides in the synthesis of purine nucleosides
3.4
589
2.8 n-Pentenyl Furanoside Donors
2.8.1 Chemoselective Deprotection of the Anomeric Center
Unlike n-pentenyl pyranosides, the corresponding furanosides have attracted comparatively
little attention. Sharma and Rao reported the preparation of n-pentenyl D-allo-, and D-gulofuranosides 143 and 146, respectively ( > Scheme 19) [55]. They made use of an efficient acidinduced rearrangement of diacetonides 142 and 145, in the presence of n-pentenyl alcohol. The
ensuing pent-4-enyl diacetonides 143 and 146, were chemoselectively cleaved to hemiacetals
144 and 147.
⊡ Scheme 19
Pent-4-enyl furanosides from D-allose and D-gulose diacetonides
⊡ Scheme 20
Pentenyl ribofuranosides in the synthesis of purine nucleosides