ISSN:
0170-2041
Keywords:
Carbohydrates
;
Cyclopropanes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Approaches to the cyclopropanated pyranosides benzyl 3,4-(“exo”-cyano)methano-3,4-dideoxy-β-(L-arabinopyranoside (5) and benzyl 3,4-(“exo”-cyano)methano-3,4-dideoxy-α-D-arabinopyranoside (6) and the branched-chain epoxy sugars benzyl 2,3-anhydro-4-(tert-butoxycarbonyl)methyl-4-deoxy-β-L-lyxopyranoside (7) and benzyl 2,3-anhydro-4-(tert-butoxycarbonyl)-methyl-4-deoxy-α-D-lyxopyranoside (8) by displacement of the triflate group with carbanions are described. Preparation of biologically important sugars bearing peptides has been demonstrated by reduction of 5 and 6 to benzyl 3,4-(“exo”-aminomethyl)methano-3,4-dideoxy-α-L-arabinopyanoside (9) and benzyl 3,4-(“exo”-aminomethyl)methano-3,4-dideoxy-α-D-arabinopyranoside (10) and the coupling of the resulting amines with protected L-alanine.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900173
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