Papulacandins和chaetiacandin：通过钯介导的4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-1-三丁基-锡烷基-D-葡糖基糖基化到其基本骨架的立体选择性途径。,Carbohydrate Research

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Papulacandins和chaetiacandin：通过钯介导的4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-1-三丁基-锡烷基-D-葡糖基糖基化到其基本骨架的立体选择性途径。
Carbohydrate Research ( IF 2.4 ) Pub Date : 1992 Jan
Dubois, E, Beau, J M

钯（0）催化的1,5-脱水-4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-2-脱氧-1-三丁基锡烷基-D-阿拉伯糖基-己-1-烯基（7 ）用3,5-二苄氧基-2-溴苄醇得到1,1（2）-脱水-4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-2-脱氧-1-（4,6-二苄氧基-2-羟甲基-苯基）-α-D-阿拉伯-己基吡喃酮e（13）。由碳酸钠缓冲的相同反应提供了1,5-脱水-4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-2-脱氧-1-（4,6-二苄氧基+++-2-羟甲基-苯基）-D-阿拉伯糖己糖-1-烯醇（11）。11的立体选择性氧化螺缩醛缩醛提供1,1（2）-脱水-4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-1-（4,6-二苄基氧基-2-羟甲基-苯基）-α- D-吡喃葡萄糖（15），木瓜素的基本三环结构。在模型研究中，将15分三步转换为1

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Papulacandins and chaetiacandin: a stereoselective route to their basic skeleton by a palladium-mediated arylation of 4,6-O-benzylidene-3-O-tert- butyldimethylsilyl-l-tributyl-stannyl-D-glucal.

Palladium(0)-catalysed coupling of 1,5-anhydro-4,6-O-benzylidene-3-O-tert- butyldimethylsilyl-2-deoxy-1-tributylstannyl-D-arabino-hex-1-eni tol (7) with 3,5-dibenzyloxy-2-bromobenzyl alcohol gave 1,1(2)-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-( 4,6- dibenzyloxy-2-hydroxymethyl-phenyl)-alpha-D-arabino-hexopyranos e (13). The same reaction buffered by sodium carbonate provided 1,5-anhydro-4,6- O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy+ ++-2- hydroxymethyl-phenyl)-D-arabino-hex-1-enitol (11). Stereoselective oxidative spiroacetalisation of 11 provided 1,1(2)- anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-(4,6-dibenzyl oxy-2- hydroxymethyl-phenyl)-alpha-D-glucopyranose (15), the basic tricyclic structure of papulacandins. In a model study, 15 was converted in three steps into 1,1(2)-anhydro-1-(4,6-dihydroxy-2-hydroxymethylphenyl)-3-O- octadecanoyl-alpha-D-glucopyranose (24), a structural analogue of papulacandin D. Moreover, stereoselective hydroboration-oxidation of 11 furnished 2-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-beta-D- glucopyranosyl)-3,5-dibenzyloxy-1-hydroxymethylbenzene (26), the structural skeleton of the chaetiacandin 3.

更新日期：2017-01-31

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