Selective Glycosylation with the Amino Sugar  D ‐Forosamine for the Synthesis of Spinosyns and Its Analogues | Zendy

Tietze Lutz F. | Zendy; Dietz Simone | Zendy; Schützenmeister Nina | Zendy; Biller Simon | Zendy; Hierold Judith | Zendy; Scheffer Timo | Zendy; Baag Mohammad M. | Zendy

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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.

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