Compound Q&A
How is (2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate (CAS: 15548-60-4) typically synthesized?
Answer
![(2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate](https://static.chemtradehub.com/structs/155/15548-60-4-86b6.webp "(2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate")
This compound is typically synthesized through a multistep process involving the protection of the indole ring, followed by introduction of the bromo and chloro substituents, and subsequent coupling with a tetrahydro-2H-pyran derivative. The synthesis involves the use of protecting groups, such as tert-butyldimethylsilyl (TBS) group, and the use of base catalysts like sodium hydride. The overall yield is moderate, around 50-60%.
About
CAS No
15548-60-4
English Name
(2R,3R,4S,5S,6R)-3-[(5-Bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-olate
Molecular Formula
C14H14BrClNO6
Molecular Weight
408.6320000000001 g/mol
SMILES
C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)O)O)O)Cl)Br
InChIKey
VFKCDXJDSDJFQU-LNNRFACYSA-N
Last Updated: 2025-10-10 21:10
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