Tetrahedron p. 4829 - 4838 (1996)
Update date:2022-08-04
Topics:
Spanu, Pietro
Rassu, Gloria
Ulgheri, Fausta
Zanardi, Franca
Battistini, Lucia
Casiraghi, Giovanni
A new efficient synthesis of 3-amino-3-deoxy-D-altrose (13), 3-amino-3-deoxy-L-allose (17), and 4-amino-4-deoxy-D-talose (21) from 2,3-O-isopropylidene-D-glyceraldehyde (6) using N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as homologative nucleophile is described. The procedure highlights the merits of densely functionalized homochiral heptonolactam 9 as a key divergent intermediate.
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