CAS: 72741-87-8; Swainsonine

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在 盐酸,Lithium Aluminium Tetrahydride体系中,用 甲醇,四氢呋喃 作为反应溶剂,化学反应 11.0H,以90%的收率获得产物八倾吲嗪三醇
参考文献:一种制备苦马豆素[(-)-Swainsonine]的方法
标题:一种制备苦马豆素[(-)-Swainsonine]的方法
摘要:本发明属于化学合成领域,涉及具有抗癌活性苦马豆素[(‑)‑swainsonine]的制备方法.本发明所述制备苦马豆素[(‑)‑swainsonine]的技术路线,操作简单,路线简洁,收率较高,所用的试剂均为常用试剂.本发明方法制备苦马豆素[(‑)‑swainsonine]的成本能明显降低,在实验室中可方便实现10‑100克级的制备,可适合大规模制备.

专利信息

专利号:US-5187279-A
优先权日:1990-07-27
标题:Synthesis of (-) swainsonine and intermediate compounds employed in such synthesis
发明人：CHA JIN K; BENNETT III RICHARD B
权利人:CHA JIN K; BENNETT III RICHARD B
摘要:(-)-Swainsonine is prepared by the steps of first reacting a compound having the formula: ##STR1## wherein each R 2 is lower alkyl, with (4-carbalkoxybutyl) triphenylphosphonium bromide in a strong base to obtain an alcohol having the formula: ##STR2## wherein R 2 is as defined above and R is C 1 -C 8 alkyl; the alcohol is then reacted with methanesulfonyl chloride or p-toluenesulfonyl chloride or benzenesulfonyl chloride in the presence of a tertiary amine to obtain the corresponding sulfonate. Heating the sulfonate with an azide in an organic solvent yields an imine having the formula: ##STR3## wherein R 2 and R are ad defined above. Treating the imine with an inorganic base, in aqueous alcohol provides upon acidification, the corresponding acid. Heating the acid at reflux temperature in organic solvent, yields an enamide having the formula: ##STR4## wherein R 2 is as defined above. Treating the enamide with diborane followed by reaction with hydrogen peroxide provides a protected swainsonine having the formula: ##STR5## which upon acid hydrolysis gives swainsonine.

专利号:WO-9006311-A1
优先权日:1988-11-29
标 题 :Synthesis of (-)-swainsonine and intermediate compounds employed in such synthesis
发明人：CHA JIN KUN; BENNETT RICHARD BERNARD III
权利人:UNIV VANDERBILT
摘要:A method of synthesizing swainsonine and its analogues employing a unique intermediate imine and a unique intermediate enamide.

专利号:US-5484925-A
优先权日:1990-07-27
标题:Synthesis of (-)-swainsonine and intermediate compounds employed in such synthesis
发明人：CHA JIN K; BENNETT III RICHARD B
摘要:Enamides of the formula: ##STR1## wherein each R 2 when taken independently represents alkoxymethyl or arylmethyl and when taken together represent alkylene bridging the oxygen atoms to which they are bonded; and R 3 represents oxygen or hydrogen; are described as useful intermediates in a process for preparing swainsonine.

专利号:WO-2023008461-A1
优先权日:2021-07-27
标题:Medicament for treatment and/or prevention of cancer
发明人：KUME MASAHIKO; OKANO FUMIYOSHI; SAITO TAKANORI
权利人:TORAY INDUSTRIES
摘要:The present invention relates to a medicament for the treatment and/or prevention of cancer, the medicament being characterized by comprising an antibody having an immunological reactivity with CAPRIN-1 protein or a fragment of the antibody and a drug capable of inhibiting the N-glycoside-linked sugar chain synthesis of a glycoprotein which are combined with each other in a blended or separated form.

专利号:US-2007293456-A9
优先权日:2004-12-30
标题:Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds
发明人：HAYFORD ANTHONY; KALOKO JOSEPH
权利人:HAYFORD ANTHONY; KALOKO JOSEPH
摘要:A method of making a compound of Formula I: n n ncomprises reacting a compound of Formula II n n nwith a compound such as R 1 OH or R 1 SH, to produce said compound of Formula I. Compounds of Formula I are useful, among other things, as dyes, spectral sensitizers, glycosidase inhibitors, and as antibacterial, antiviral, and anti-inflammatory agents.

专利号:US-6051711-A
优先权日:1997-10-24
标 题 :Synthesis of swainsonine salts
发明人：TROPPER FRANCOIS; SHAH RAJAN N; SHARMA PRADEEP
权利人:GLYCODESIGN INC
摘要:A method for synthesizing swainsonine salts and intermediates thereof comprising subjecting a compound of the formula I wherein R2 and R2' are the same or different and represent alkyl, halogen, alkenyl, alkoxy, cycloalkyl or aryl which may be substituted, to acid hydrolysis in the presence of a C1-4 alkanol to obtain a crystalline salt of swainsonine; and optionally, recrystallizing the swainsonine salt from a C1-4 alkanol. The reaction may be used in combination with one or more additional reaction steps.