76768-53-1

Upstream product

• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 68963-23-5 1-hydroxy-7-methylanthracene-9,10-dione 

Relevant academic research and scientific papers

Highly Regio- and Stereo-selective Diels-Alder Reactions of 5-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)-1,4-naphthoquinone

The title compound 1b reacts with cyclopentadiene to give a single cycloadduct, assigned the stereostructure 6a by X-ray crystallography; single cycloadducts, i.e. 4c and d, also arise in the corresponding reactions involving the dienes 2b and c.

Asymmetric Diels-Alder Reactions. Part 6. Regio- and Stereo-selective Cycloadditions of 5-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)-1,4-naphthoquinone

The title naphthoquinone 1d underwent reaction with cyclopentadiene to give a cycloadduct, established as (1R,4S,4aR,9aS)-1,4,4a,9a-tetrahydro-5-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-1,4-methano-9,10-anthraquinone 9a by X-ray crystallographic analysis.Single cycloadducts, assigned the structures 4d, 4e and 17 were also isolated from the reactions of the naphthoquinone 1d with (E)-1-methoxy-3-trimethylsiloxybuta-1,3-diene 2b, (E)-3-methyl-1-trimethylsiloxybuta-1,3-diene 2f and (E)-2-methyl-1-trimethylsiloxybuta-1,3-diene 16.A 2:1 mixture of cycloadducts, formulated as the regioisomers 4g and 3f, arose in the reaction of the dienophile 1d with (E)-1-acetoxy-3-methylbuta-1,3-diene 2g. The sugar auxiliary was readily detached from the oxidation product of compound 9a, i.e. (1R,4S)-1,4-dihydro-5-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-1,4-methano-9,10-anthraquinone 18b, by acidic hydrolysis to give the aglycone 18a. An X-ray crystallographic analysis of compound 1d revealed that the quinone ring adopts a boat-like geometry in which the carbonyl oxygen atoms shield the syn-face of the C(2)-C(3) double bond. endo-Addition of dienes to the anti-face provides an explanation for the high diastereofacial reactivity of the naphthoquinone 1d.

GLUCOSIDATION OF 2-HYDROXY- AND 5-HYDROXY-1,4-NAPHTHOQUINONE

Using the Koenigs-Knorr method two isomeric monohydroxynaphthoquinones were glucosidized, i.e. 2-hydroxy-1,4-naphthoquinone (lawson, Ia) and 5-hydroxy-1,4-naphthoquinone (juglone, IIa).The structure of the corresponding glucosides Ib and IIb was proved by 1H-NMR, mass, UV, VIS and IR spectra.