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Selective Glycosylation with the Amino Sugar D ‐Forosamine for the Synthesis of Spinosyns and Its Analogues
Author(s) -
Tietze Lutz F.,
Dietz Simone,
Schützenmeister Nina,
Biller Simon,
Hierold Judith,
Scheffer Timo,
Baag Mohammad M.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300983
Subject(s) - chemistry , glycosylation , sugar , glycoside , selectivity , alcohol , amino sugar , stereochemistry , organic chemistry , iodine , biochemistry , catalysis
For the synthesis of novel spinosyn analogues, the selective introduction of the 2‐deoxyamino sugar, D ‐forosamine, necessary for their bioactivity, is described. The reactions of different alcohol acceptors with the D ‐forosamine donor in the presence of iodine and Et 3 SiH gave the corresponding glycosides in yields of up to 96 % and with an α/β selectivity of 2:3.