ChemicalBook CAS DataBase List Cassiaside C

Cassiaside C synthesis

3synthesis methods

Product Name:Cassiaside C
CAS Number:119170-52-4
Molecular formula:C27H32O15
Molecular Weight:596.54

1.Add Ag2CO3 (414 mg, 1.50 mmol) to a stirring suspension of 2,3,4-tri-O-benzoyl-6-O-acetyl-D-glucopyranosyl bromide (6d, 596 mg, 1.00 mmol) in acetone (10 mL) and water (0.5 mL) portionwise.2.After stirring for 40 minutes at ambient temperature, filter the mixture through a pad of Celite.3.Wash the filtrate with acetone.4.Dry the filtrate.5.Concentrate the filtrate.6.Purify the residue by column chromatography (petroleum ether-EtOAc, 3:1).

1H-Naphtho[2,3-c]pyran-1-one, 10-hydroxy-7,9-dimethoxy-3-methyl-

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Yield:-

Steps:

Multi-step reaction with 5 steps
1: 85 percent / BBr₃ / CH₂Cl₂ / 7 h / 20 °C
2: tetrabutylammonium bromide; borate buffer / CHCl₃ / 12 h / 52 °C / pH 10.8
3: 85 percent / aq. HCl / methanol; CH₂Cl₂ / 18 h / 20 °C
4: 92 percent / TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 4 h / 0 - 20 °C
5: 97 percent / K₂CO₃ / tetrahydrofuran; methanol / 20 h / 20 °C

References:

Zhang, Zhaojun;Yu, Biao [Journal of Organic Chemistry,2003,vol. 68,# 16,p. 6309 - 6313]

1,4-Cyclohexadiene-1,2-dicarbonitrile, 4-chloro-3,6-dioxo-

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References

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References

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