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Synthesis of cyclo Sal‐(Glycopyranosyl‐6)‐phosphates as Activated Sugar Phosphates
Author(s) -
Huchting Johanna,
Ruthenbeck Alexandra,
Meier Chris
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.201300852
Subject(s) - chemistry , regioselectivity , ether , protecting group , silyl ether , isomerization , tetra , chloride , medicinal chemistry , organic chemistry , catalysis , silylation , stereochemistry , alkyl
The synthesis of cyclo Sal‐masked glycopyranosyl phosphates demands suitably protected precursors. A highly regioselective strategy for the preparation of cyclo Sal‐(1,2,3,4‐tetra‐ O ‐acetylglycopyranosyl‐6)‐phosphates was developed. Intermediate introduction of the Fmoc‐group allowed the isolation of the 1,2,3,4‐tetra‐ O ‐acetyl glycopyranoses to be skipped, thus, no isomerization occurred. Glycopyranoses were first converted into the 6‐ O ‐TBDMS‐1,2,3,4‐tetra‐ O ‐acetyl derivatives then, in a one‐pot reaction, the silyl ether was cleaved and the resulting 1,2,3,4‐tetra‐ O ‐acetyl glycopyranoses were trapped with Fmoc‐chloride. In this exchange of protecting groups no acetyl group migration occurred. The 6‐ O ‐Fmoc‐protected intermediates were selectively converted into the cyclo Sal‐masked glycopyranosyl phosphates in a one‐pot reaction. Finally, the reactivity of these activated glycopyranosyl‐6‐phosphates was demonstrated in the synthesis of 1,6‐diglycopyranosyl‐phosphates.