A new procedure for the preparation of beta-keto-delta-lactones from sugars and their transformation into glycosyl acceptors in disaccharides synthesis
Org Lett
; 2(3): 251-3, 2000 Feb 10.
Article
in En
| MEDLINE
| ID: mdl-10814294
ABSTRACT
[reaction see text] Glycals are effective starting materials for the synthesis of enantiopure beta-ketone-delta-lactones. They are easily transformed, through a two-step, one-pot reaction, into the corresponding alpha,alpha'-dioxothiones which in turn can be quantitatively trapped with dienophiles in inverse electron-demand [4 + 2] cycloadditions. The reaction of dioxothione 8b with endo and exo glucals allowed the elaboration of a new protocol to prepare 2-thio- or 2-deoxydisaccharides stereoselectively.
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Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2000
Type:
Article
Affiliation country:
Italy