CAS: 130525-58-5; (1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-Azido-6-(Methoxycarbonyl)-3,4-Dihydro-2H-Pyran-2-yl)Propane-1,2,3-Triyl Triacetate

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在 2,2,6,6-Tetramethyl-Piperidine-N-Oxyl,Calcium Hypochlorite 吡啶,盐酸,四氧化锇,Sodium Azide,氢氟酸,四丁基溴化铵,氨,水,Lithium,Sodium Hydride,碳酸氢钠,Potassium Carbonate,氯化铵,戴斯-马丁氧化剂,N-甲基吗啉氧化物,1,8-二氮杂双环[5.4.0]十一碳-7-烯,三乙胺,Potassium Bromide体系中,用 四氢呋喃,乙醚,乙醇,二氯甲烷,N,N-二甲基甲酰胺,丙酮,乙腈,叔丁醇 用作溶剂,化学反应 124.5H,反应生成5-乙酰氨基-7,8,9-O-三乙酰基-2,6-脱水-4-叠氮-3,4,5-三脱氧-D-甘油-D-半乳-2-壬烯酸甲酯
参考文献:4-叠氮基-4-脱氧-Neu5,7,8,9Ac42En1Me的合成.由d-葡萄糖酸-δ-内酯合成gg167的关键中间体.
标题:4-叠氮基-4-脱氧-Neu5,7,8,9Ac42En1Me的合成.由d-葡萄糖酸-δ-内酯合成gg167的关键中间体.
摘要:[反应:见正文] 5-乙酰氨基7,8,9-三-O-乙酰基-2,6-脱水4-叠氮基-3,4,5-三苯氧基-D-甘油-D-Gal的立体选择性合成以d-葡萄糖酸-δ-内酯为起始原料,合成了神经氨酸酶抑制剂gg167(zanamivir,Relenza)的高级关键中间体,Acton-Non-2-Enonic Acid甲基酯.亚胺中间体的高度非对映选择性烯丙基化,氮丙啶的区域选择性叠氮化物开口以及邻位二醇的化学选择性氧化成功地用作关键步骤.
Doi:10.1021/ol0491890

专利信息

专利号:US-8993789-B2
优先权日:2008-11-28
标题:Process for preparing zanamivir and intermediates for use in the process
发明人：PHULL MANJINDER SINGH; KANKAN RAJENDRA NARAYANRAO; RAO DHARMARAJ RAMACHANDRA; SAWANT ASHWINI AMOL; THOPPIL SANOJ
权利人:PHULL MANJINDER SINGH; KANKAN RAJENDRA NARAYANRAO; RAO DHARMARAJ RAMACHANDRA; SAWANT ASHWINI AMOL; THOPPIL SANOJ; CIPLA LTD
摘要:The present invention provides a process for preparing methyl 5-acetamido-4-amino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (V), which process comprises reducing methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (IV) in the presence of a reducing agent selected from the group consisting of lithium aluminum hydride, sodium borohydride, zinc/ammonium chloride, zinc-ferric chloride and ferric chloride/sodium iodide. The present invention also provides compounds of formula (VIII) and (IX) which may be used in the synthesis of zanamivir. The present invention also provides processes for preparing compounds (VIII) and (IX) and processes involving their use, including in the synthesis of zanamivir.