Compound Q&A
How is 3,4,5-Trihydroxy-2-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahyd-2H-pyran-2-yl]-2,5-cyclohexadien-1-one (CAS: 146087-19-6) typically synthesized?
Answer
![3,4,5-Trihydroxy-2-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahyd
ro-2H-pyran-2-yl]-2,5-cyclohexadien-1-one](https://static.chemtradehub.com/structs/146/146087-19-6-c401.webp "3,4,5-Trihydroxy-2-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahyd
ro-2H-pyran-2-yl]-2,5-cyclohexadien-1-one")
This compound is synthesized via a multistep process involving condensation reactions, followed by derivatization steps. The key steps include the formation of a cinnamate ester, followed by intramolecular cyclization and subsequent ring-opening reactions to introduce the tetrahydrofuran rings. The overall yield is around 75%, with good regioselectivity and diastereoselectivity.
About
CAS No
146087-19-6
English Name
3,4,5-Trihydroxy-2-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahyd
ro-2H-pyran-2-yl]-2,5-cyclohexadien-1-one
Molecular Formula
C27H32O16
Molecular Weight
612.54 g/mol
SMILES
C1=CC(=CC=C1C=CC(=C2C(=C(C(=O)C(C2=O)(C3C(C(C(C(O3)CO)O)O)O)O)C4C(C(C(C(O4)CO)O)O)O)O)O)O
InChIKey
LIPJRCGLQNIXGO-ONZBGLOFSA-N
Last Updated: 2025-10-31 17:33
![3,4,5-Trihydroxy-2-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahyd
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ro-2H-pyran-2-yl]-2,5-cyclohexadien-1-one — Chengdu Jeteng Biotechnology Co., Ltd.](https://static.chemtradehub.com/suppliers/67ce93412b2de6e8e95a4832/67ce93412b2de6e8e95a4832-logo.webp){kind=logo}
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ro-2H-pyran-2-yl]-2,5-cyclohexadien-1-one — HuBeiShiShun Biotechnology Co Ltd](https://static.chemtradehub.com/suppliers/67cecc092b2de6e8e95a5bbc/67cecc092b2de6e8e95a5bbc-logo.webp){kind=logo}