CAS: 83-48-7; (3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-Ethyl-6-Methylhept-3-En-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-Ol

该化合物是各种植物来源,包括大豆和卡勒巴豆中发现的一种植物激素,它是合成类固醇激素,维生素D3和其他生物活性化合物的前体,其化学结构在C22位置上具有双重联系,有别于象β-西托斯特罗等其他酯醇.Stigmasterol因其在制药和养分应用,特别是在胆固醇管理和抗炎研究方面的作用而受到重视.它具有潜在的抗氧化特性,并研究其对脂质代谢的影响.该化合物通常通过溶剂提取或染色法分离,确保工业和研究用途的高度纯度.其稳定性和生物利用率使它在有机合成中成为多用途的中间体.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

tert-butyl(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-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)dimethylsilane stigmasterol methyl ether (23S,24R,25R)-23-ethyl-24,26-cycl°Cholest-5-en-3β-ol (2-{1-[(3S,8S,9S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-ethoxy}-ethyl)-trimethyl-silanet-diene3β-(3-bromo-benzoyloxy)-stigmasta-5,22t-diene t-diene3β-(4-nitro-phenylcarbamoyloxy)-stigmasta-5,22t-diene p-tolylcarbamoyloxy-stigmasta-5,22t-diene3β-p-tolylcarbamoyloxy-stigmasta-5,22t-diene o-tolylcarbamoyloxy-stigmasta-5,22t-diene3β-o-tolylcarbamoyloxy-stigmasta-5,22t-diene

合成工艺路线路线简述

  • 合成目标产物 Stigmasterol 主要起始原料 3,5-Cyclo-27-Norcholest-23-En-22-Ol, 6-Methoxy-, (3β,5α,6β,22R,23Z)- (9CI)
  • 122795-00-0 = 83-48-7
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Hexamethylphosphoramide
    标题:Reductive Cleavage Of Tert-Butyldimethylsilyl Ethers With Sodium Hydride
    作者:Shekhani,Mohammed Saleh; Et Al
    参考文献:Tetrahedron Letters 日期:1988 卷标:29(47) 页码:6161-2]

    = 83-48-7
    反应条件:1.1 Catalysts: Azobisisobutyronitrile,Pentafluorobenzenethiol Solvents: Chlorobenzene; Rt -> 80 °C; 3 H,80 °C
    标题:Thiol Catalyzed Aerobic Debenzylation Of Alcohols And Amines
    作者:Lardy,Samuel W.; Et Al
    参考文献:Chemrxiv 日期:2021 卷标:1 页码:1-12]

    913191-42-1 = 83-48-7
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol; Overnight,Rt
    标题:Two New Steroids Dehydroadynerizoside And Neristigmol From Nerium Oleander Leaves
    作者:Siddiqui,B. S.; Et Al
    参考文献:Polish Journal Of Chemistry 日期:2006 卷标:80(3) 页码:445-452]

    15072-97-6 = 83-48-7 + 58274-46-7
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Methyl Ethyl Ketone,Water
    标题:Synthesis Of Brassinolide. Part Ii. A Simple Synthesis Of Steroidal 3α,5-Cyclo-6-Ones And Their Efficient Transformation To Steroidal 2-En-6-Ones
    作者:Aburatani,Masakazu; Et Al
    参考文献:Synthesis 日期:1987 卷标:(2) 页码:181-3]

    19716-26-8 = 83-48-7 + 50-99-7
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Reflux
    标题:A New 3,4-Seco-Lupane Derivative From Lasianthus Gardneri
    作者:Dallavalle,Sabrina; Et Al
    参考文献:Journal Of Natural Products 日期:2004 卷标:67(5) 页码:911-913]

    4651-48-3 = 83-48-7
    反应条件:1.1 Catalysts: Dibutyltin Oxide Solvents: Methanol,Chloroform; 6 H,50 °C
    标题:Mild And Selective Deprotection Method Of Acetylated Steroids And Diterpenes By Dibutyltin Oxide
    作者:Wang,Shao-Min; Et Al
    参考文献:Steroids 日期:2007 卷标:72(1) 页码:26-30]

    53139-42-7 = 83-48-7 + 103881-47-6
    反应条件:1.1 Reagents: Potassium Bicarbonate Solvents: Acetone,Water; 6 H,Reflux
    标题:Improvement Of Synthetic Method Of Brassinosteroids
    作者:Ruensamran,Wanwikar; Et Al
    参考文献:Kamphaengsaen International Natural Products Symposium: The Relationship Between Living Organisms And Environment 日期:2010 卷标:208 页码:208-215]

    51529-12-5 = 83-48-7
    反应条件:1.1 Reagents: Potassium Tert-Butoxide Catalysts: 2982793-44-0; 48 H,120 °C
    标题:Triazole Backbone Ligand In An Unprecedented Efficient Manganese Catalyst For Use In Transfer Hydrogenation
    作者:Liang,Qianqian; Et Al
    参考文献:Science China: Chemistry 日期:2023 卷标:66(7) 页码:2028-2036]

    83-48-7 = 83-48-7 + 58274-46-7
    反应条件:1.1 Reagents: Triethylamine Solvents: Methyl Ethyl Ketone2.1 Reagents: Sodium Bicarbonate Solvents: Methyl Ethyl Ketone,Water
    标题:Synthesis Of Brassinolide. Part Ii. A Simple Synthesis Of Steroidal 3α,5-Cyclo-6-Ones And Their Efficient Transformation To Steroidal 2-En-6-Ones
    作者:Aburatani,Masakazu; Et Al
    参考文献:Synthesis 日期:1987 卷标:(2) 页码:181-3
醋酸豆甾醇置于二正丁基氧化锡体系中,用 甲醇,氯仿 作为反应溶剂,化学反应 6.0H,以10%的收率获得产物豆甾醇
参考文献:Mild And Selective Deprotection Method Of Acetylated Steroids And Diterpenes By Dibutyltin Oxide
标题:Mild And Selective Deprotection Method Of Acetylated Steroids And Diterpenes By Dibutyltin Oxide
摘要:Dibutyltin Oxide (Dbto) Was First Utilized For The Deacetylation Of Steroid And Diterpene Esters. The Results Showed The Deprotection Of Acetylated Steroids And Diterpenes Separately With Moderate Catalysis Dibutyltin Oxide In Methanol Selectively Removed Part Acetyl Groups Of These Substrates,Whereas Several Functional Groups Of The Steroids And Diterpenes Were Retained And Neither Isomerization Nor Degradation Of These Substrates Was Observed. It Seems That The Acetyl Groups With Lower Steric Hindrance Or Near Carbonyl,Alkoxy,Or Hydroxyl Groups Can Be Cleaved By The Reaction,Whereas The Acetyl Groups With Higher Steric Hindrance Or Without Carbonyl,Alkoxy,Or Hydroxyl Groups Neighboring Were Retained Under The Same Conditions. One Of The Interesting Results Obtained Was The Selective Hydrolysis Of The 3 Beta-O-Acetyl Group In The Presence Of The 6 Beta Group In 3 Beta,6 Beta-Di-O-Acetyl-5 Alpha-Hydroxypregn-16-En-20-One. This Allows For Subsequent Introduction Of One Unit At C-3 And The Other Unit At C-6. This Procedure Is Useful For The Synthesis Of A Series Of Closely Related Isomers Of 3 Beta,5 Alpha,6 Beta-Trihydroxypregn-16-En-20-One And Other Widespread Polyhydroxysteroids In Marine Organisms And Some Terrestrial Species. (C) 2006 Elsevier Inc. All Rights Reserved.
DOI:10.1016/j.Steroids.2006.10.004

海关参考信息

专利信息


专利号:US-2008032964-A1
优先权日:2006-04-10
标题:Process for the synthesis of azetidinone
发明人:KANSAL VINOD K; AHMAD SUHAIL; MARIAPPAN SHANMUGAVEL; TYAGI BHUPENDRA; PERLMAN NURIT; LE PAIH JACQUES; ZANOTTI-GEROSA ANTONIO
权利人:KANSAL VINOD K; AHMAD SUHAIL; MARIAPPAN SHANMUGAVEL; TYAGI BHUPENDRA; PERLMAN NURIT; LE PAIH JACQUES; ZANOTTI-GEROSA ANTONIO
摘要:Provided are intermediates useful for the synthesis of hydroxyl-alkyl substituted azetidinones, processes of their preparation, and processes for the synthesis of certain hydroxyl-alkyl substituted azetidinones. Also provided are processes for the synthesis of 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone, or ezetimibe.

专利号:US-11479577-B2
优先权日:2016-05-18
标题:Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid
发明人:WEYMOUTH-WILSON ALEXANDER; KOMSTA ZOFIA; WALLIS LAURA; EVANS TIMOTHY; DAVIES IEUAN; OTTER CARL; BATCHELOR RHYS
权利人:NZP UK LTD
摘要:The present invention relates to compounds which are intermediates in the synthesis of bile acid derivatives with pharmacological activity. The invention relates to compounds of general formula (I):wherein:, R1, R2, R3, R4, R5, R6 and Y are as defined herein.The compounds are intermediates in the synthesis of synthetic bile acids which are useful in the treatment of conditions such as liver disease. In addition, the invention relates to a method of synthesizing these intermediates and a method of preparing obeticholic acid and obeticholic acid analogues from the compounds of the invention.

专利号:US-4226770-A
优先权日:1978-02-10
标题:Synthesis of steroids
发明人:KAISER EMIL T
权利人:KAISER EMIL T
摘要:The synthesis of 1α,25-dihydroxycholesterol, 1α,25-dihydroxy-7-dehydrocholesterol and 1α,25-dihydroxycholecalciferol and other sterol derivatives from bile acids. Also the synthesis of 3,6-diketo steroids useful in the production of 1α,25-dihydroxycholesterol and other sterols which are biologically active or can be converted to biologically active sterols. The invention involves the sterols so produced and the processes by which they are prepared.

专利号:US-4163744-A
优先权日:1978-02-10
标 题:Synthesis of steroids
发明人:KAISER EMIL T
权利人:KAISER EMIL T
摘要:The synthesis of 1α,25-dihydroxycholesterol, 1α,25-dihydroxy-7-dehydrocholesterol and 1α,25-dihydroxycholecalciferol and other sterol derivatives from bile acids. Also the synthesis of 3,6-diketo steroids useful in the production of 1α,25-dihydroxycholesterol and other sterols which are biologically active or can be converted to biologically active sterols. The invention involves the sterols so produced and the processes by which they are prepared.

专利号:US-9943544-B2
优先权日:2015-03-18
标 题:Process for bio synthesis of nano arsenic trioxide and its use in treatment of diseases including cancer
发明人:BENDALE YOGESH NARAYAN; BENDALE VINEETA YOGESH
权利人:BENDALE YOGESH NARAYAN; BENDALE VINEETA YOGESH
摘要:The present invention is a process for bio synthesis of nano arsenic trioxide defined by its low toxicity, higher bio availability and nano particle size with the aid of buttermilk, goat urine, dolichos biflorous and other plant materials such as ginger, momordica charantia and musa paradisiaca . The invention is carried out in different steps involving purification of crude form of arsenic trioxide by boiling it with buttermilk, goat urine and extract of dolichos biflorous in subsequent steps, followed by the trituration of the bio purified arsenic trioxide with extracts of ginger and momordica charantia in subsequent steps and heating of the dry product obtained after trituration with musa paradisiaca resulting in the production of novel nano arsenic trioxide. The product is effective in the treatment of various diseases including different types of cancer in animals and humans. The product obtained through the process is less toxic with higher bio availability.

专利号:WO-2021019558-A1
优先权日:2019-07-30
标题 :An efficient method for synthesis of 5-(3-pyridyl)-2,2'-bithiophene(sensitizer)
发明人:DATLA ANUPAMA; NAGRE PRASHANT; TAMORE JAGDISH; PRABHU MANOJKUMAR SADANAND; KADAM SACHIN VASANT
权利人:FERMENTA BIOTECH LTD
摘要:The present invention discloses an efficient process for synthesis of photosensitizer, 5-(3-pyridyl)-2,2'-bithiophene in high yield and purity.
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参考文献:10.1007/s00299-011-1119-6
摘要:Burlini N, Iriti M, Daghetti A, Faoro F, Ruggiero A, Bernasconi S. Benzothiadiazole (BTH) activates sterol pathway and affects vitamin D3 metabolism in Solanum malacoxylon cell cultures. Plant Cell Rep. 2011 Nov;30(11):2131–41. doi: 10.1007/s00299-011-1119-6.
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