b-Sitosterol (b-sitosterol) ,Aka(3b)-Stigmasterol-5-Alkene-3-alcohol,yesPhytosterolsOne of class components,It belongs to tetracyclic triterpenoid compounds,It widely exists in all kinds of naturalvegetable oil\NutsAmong other plant seeds,Also found in some botanical drugs.at present β-Sitosterol is widely used in the pharmaceutical industry due to its unique biological and physicochemical properties,In particular, studies have shown that β-The intake of sitosterol is related to the incidence of many chronic diseases in the population,Studies have shown that it can significantly reduce the serumcholesterolEfficacy of,Can replace cholesterol as liposome membrane material.
Synthetic Circuit 1
1.1
Reagents:
Aluminum iodide
Solvents:
Acetonitrile
,
Dichloromethane
;
10 min, rt
1.2
Reagents:
Sodium thiosulfate
Solvents:
Water
2.1
Reagents:
Potassium carbonate
Solvents:
Methanol
,
Dichloromethane
;
12 h, rt
Reference
A concise synthesis of β-sitosterol and other phytosterols
Hang, Jiliang; et al,
Steroids,
2010,
75(12),
879-883
Synthetic Circuit 2
1.1
Reagents:
Sulfuric acid
Solvents:
Water
;
5 h, reflux
Reference
β-sitosterol-3-O-β-D-xylopyranosyl (1→4)-O-β-D-glucopyranoside from the seeds of Zanthoxylum hamiltonianum Wall
Rajpoot, Sandhya,
International Journal of Chemical Sciences,
2013,
11(2),
1131-1136
Synthetic Circuit 3
1.1
Catalysts:
Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(OH)2O10.xH2O)
Solvents:
Methanol
Reference
Montmorillonite clays catalysis. IX. A mild and efficient method for removal of tetrahydropyranyl ethers
Li, Tong-Shuang; et al,
Synthetic Communications,
1999,
29(2),
181-188
Synthetic Circuit 4
1.1
Reagents:
Ethanol
Catalysts:
μ4-Oxohexakis[μ-(2,2,2-trifluoroacetato-κO:κO′)]tetrazinc
;
96 h, reflux
Reference
A tetranuclear-zinc-cluster-catalyzed practical and versatile deprotection of acetates and benzoates
Iwasaki, Takanori; et al,
Chemistry - A European Journal,
2010,
16(38),
11567-11571
Synthetic Circuit 5
Reference
Phytochemical study of privet (Ligustrum vulgare L.)
Diak, J.,
Herba Polonica,
1988,
34(3),
103-8
Synthetic Circuit 6
1.1
Reagents:
Hydrochloric acid
,
Water
Solvents:
Water
Reference
Constituents of the roots of Boerhaavia diffusa L. I. Examination of sterols and structures of new rotenoids, boeravinones A and B
Kadota, Shigetoshi; et al,
Chemical & Pharmaceutical Bulletin,
1989,
37(12),
3214-20
Synthetic Circuit 7
1.1
Reagents:
Hydrogen
Catalysts:
Palladium
Solvents:
Methanol
,
Dichloromethane
;
24 h, 200 psi, 23 °C
1.2
Catalysts:
p-Toluenesulfonic acid
Solvents:
1,4-Dioxane
,
Water
;
3 h, 80 °C
Reference
Identification and characterization of β-sitosterol target proteins
Lomenick, Brett; et al,
Bioorganic & Medicinal Chemistry Letters,
2015,
25(21),
4976-4979
Synthetic Circuit 8
1.1
Catalysts:
Palladium
Solvents:
Ethanol
;
16 h, 50 psi, rt
1.2
Reagents:
p-Toluenesulfonic acid
Solvents:
1,4-Dioxane
,
Water
;
3 h, 80 °C
Reference
Synthesis, isolation and characterization of β-sitosterol and β-sitosterol oxide derivatives
McCarthy, Florence O.; et al,
Organic & Biomolecular Chemistry,
2005,
3(16),
3059-3065
Synthetic Circuit 9
1.1
Solvents:
Acetic acid
;
2 h, reflux
2.1
Reagents:
Potassium hydroxide
Solvents:
Diethyl ether
,
Methanol
;
15 h, rt
Reference
Practical and facile route to a functional intermediate from stigmasterol for the synthesis of 1α-hydroxyvitamin D5 and related compounds
Takahashi, Michiyasu; et al,
Heterocycles,
2016,
93(1),
101-113
Synthetic Circuit 10
1.1
Catalysts:
p-Toluenesulfonic acid
Solvents:
1,4-Dioxane
,
Water
;
3 h, 80 °C
Reference
Identification and characterization of β-sitosterol target proteins
Lomenick, Brett; et al,
Bioorganic & Medicinal Chemistry Letters,
2015,
25(21),
4976-4979
Synthetic Circuit 11
Reference
Configurations at C-24 of 24-alkylsterols from Clerodendrum infortunatum Linn
Thakur, Swapnadip; et al,
Indian Journal of Chemistry,
1988,
(1),
17-20
Synthetic Circuit 12
Reference
Isolation and structure of isopropyl-α-D-glucoside from the coral Sclerophytum capitalis
Sharma, Perveen; et al,
Journal of Natural Products,
1989,
52(2),
395-7
Synthetic Circuit 13
1.1
Reagents:
Potassium hydroxide
Solvents:
Ethanol
,
Water
;
8 h, reflux
Reference
Phytosterol and γ-Oryzanol Conjugates: Synthesis and Evaluation of their Antioxidant, Antiproliferative, and Anticholesterol Activities
Lesma, Giordano; et al,
Journal of Natural Products,
2018,
81(10),
2212-2221
Synthetic Circuit 14
1.1
Reagents:
Potassium carbonate
Solvents:
Methanol
,
Dichloromethane
;
12 h, rt
Reference
A concise synthesis of β-sitosterol and other phytosterols
Hang, Jiliang; et al,
Steroids,
2010,
75(12),
879-883
Synthetic Circuit 15
Reference
Sterols of Salsola collina
Syrchina, A. I.; et al,
Khimiya Prirodnykh Soedinenii,
1989,
(5),
731-2
Synthetic Circuit 16
Reference
Synthesis of triaromatic steroid hydrocarbons methylated at position 2, 3, or 6: molecular fossils of yet unknown biological origin
Lechtfouse, Eric; et al,
Tetrahedron,
1994,
50(6),
1731-44
Synthetic Circuit 17
1.1
Reagents:
Potassium hydroxide
Solvents:
Diethyl ether
,
Methanol
;
15 h, rt
Reference
Practical and facile route to a functional intermediate from stigmasterol for the synthesis of 1α-hydroxyvitamin D5 and related compounds
Takahashi, Michiyasu; et al,
Heterocycles,
2016,
93(1),
101-113
Synthetic Circuit 18
1.1
Reagents:
Pyridine
Solvents:
Methanol
;
6 h, reflux
2.1
Catalysts:
Palladium
Solvents:
Ethanol
;
16 h, 50 psi, rt
2.2
Reagents:
p-Toluenesulfonic acid
Solvents:
1,4-Dioxane
,
Water
;
3 h, 80 °C
Reference
Synthesis, isolation and characterization of β-sitosterol and β-sitosterol oxide derivatives
McCarthy, Florence O.; et al,
Organic & Biomolecular Chemistry,
2005,
3(16),
3059-3065
Synthetic Circuit 19
1.1
Reagents:
Chlorotrimethylsilane
,
Potassium fluoride (KF), dihydrate
Solvents:
Acetonitrile
;
20 min, 60 °C
1.2
Reagents:
Sodium bicarbonate
Solvents:
Water
;
rt
Reference
A mild and efficient desilylation of O-tert-butyldimethylsilyl ethers mediated by chlorotrimethylsilane and potassium fluoride dihydrate in acetonitrile
Peng, Yu; et al,
Synlett,
2006,
(8),
1165-1168
Synthetic Circuit 20
1.1
Reagents:
Potassium acetate
Solvents:
Methanol
;
3 h, reflux
2.1
Reagents:
Hydrogen
Catalysts:
Palladium
Solvents:
Methanol
,
Dichloromethane
;
24 h, 200 psi, 23 °C
2.2
Catalysts:
p-Toluenesulfonic acid
Solvents:
1,4-Dioxane
,
Water
;
3 h, 80 °C
Reference
Identification and characterization of β-sitosterol target proteins
Lomenick, Brett; et al,
Bioorganic & Medicinal Chemistry Letters,
2015,
25(21),
4976-4979