SOLASODINE synthesis
- Product Name:SOLASODINE
- CAS Number:126-17-0
- Molecular formula:C27H43NO2
- Molecular Weight:413.64
514-32-9
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126-17-0
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Yield:126-17-0 43%
Reaction Conditions:
with chloro-trimethyl-silane in dichloromethane for 12 h;Inert atmosphere;
Steps:
General procedure: Step One: following the general procedure, diosgenin acetate 1a (4.56 g, 10 mmol) wastransforemed to 17, the crude was used without purification.Step Two: using the above-mentioned condition, crude 17 was treated with freshly preparedNa (10 equiv)/naphthalene (100 equiv) to afford 36, which was used without purification.Step Three: To a solution of the crude 36 in DCM (30 mL) was added freshly distilledTMSCl (8.0 mL, 63 mmol) dropwise under argon. The mixture was stirred for 12 h, quenchedwith saturated aqueous NaHCO3 solution (100 mL), adjusted the pH value to 10 with 5%aqueous solution, and extracted with chloroform (200 mL × 2). The combined organic layerswere washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure.The residue was purified through flash column chromatography on silica gel (PE/EA: 3/1 to1/1 with 1% v/v Et3N) to give solasodine 3 (1.77 g, 43%) as a white solid.
References:
Wu, Jing-Jing;Gao, Ran;Shi, Yong;Tian, Wei-Sheng [Tetrahedron Letters,2015,vol. 56,# 47,p. 6639 - 6642] Location in patent:supporting information
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126-17-0
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$12.00/1mg
1061-54-7
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126-17-0
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126-17-0
231 suppliers
$12.00/1mg