ChemicalBook CAS DataBase List ELEUTHEROSIDE A

ELEUTHEROSIDE A synthesis

11synthesis methods

Product Name:ELEUTHEROSIDE A
CAS Number:474-58-8
Molecular formula:C35H60O6
Molecular Weight:576.86

2280-44-6

83-46-5

474-58-8

β-sitosterol (124.4 g, 0.3 mol) and D-glucose (18.0 g, 0.1 mol) were dissolved in ethylbenzene (600 mL). Trimethylsilyl trifluoromethanesulfonate (TMSOTf, 8.9 g, 7.3 mL, 40 mmol) was slowly added to the reaction system at 80 °C and the reaction was continued at a constant temperature until thin-layer chromatography (TLC) detection showed that the D-glucose was almost completely consumed (about 15 h). Upon completion of the reaction, the reaction solution was concentrated and subsequently separated by silica gel column chromatography using dichloromethane as eluent (silica gel particle size 100-200 mesh). The separation was monitored by TLC until β-sitosterol was no longer detected in the eluate, and the corresponding eluate was collected and concentrated to give the recovered β-sitosterol (83.0 g, 0.2 mol). The elution was continued with ethyl acetate as eluent and monitored by TLC until the target product (2R,3R,4S,5S,6R)-2-((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3, 4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol. Concentration of the eluate containing the target product gave a white solid product (47.3 g) in 82% yield and 97.8% purity as determined by high performance liquid chromatography (HPLC).

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Yield:474-58-8 82%

Reaction Conditions:

with trimethylsilyl trifluoromethanesulfonate in ethylbenzene at 85; for 15 h;

Steps:

9 Synthesis of daucosterol

β-sitosterol124.4g0.3mol),D-glucose (18.0 g, 0.1 mol) dissolved in ethylbenzene (600 mL).At 80°C,TMSOTf (8.9 g/7.3 mL, 40 mmol)was added and underprotection carried out constant temperature reaction until the TLC detected almost complete disappearance of D-glucose (about 15h). After the reaction was concentrated , it wassubjected to silica gel column chromatography (silica gel 100-200 mesh) using dichlromethaneas eluent. TLC assay until the eluent is free of β-sitosterol, the eluent was concentrated to give β-sitosterol(83.0g, 0.2mol), continue the elution with ethyl acetateas eluent, and TLC assay until there is no title compoundin the eluent. The eluent was concentrated to give the title compound (47.3 g) in 82% yield and HPLC purity 97.8%.

References:

CN104693266,2018,B Location in patent:Paragraph 0062-0064

83-46-5
612 suppliers
$5.00/250mg