還元生成物から2-methyl-3-formylfuranの生成 (アルミニウムアマルガムによるストレプトマイシンの還元に関する研究-1,2-)

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With the aid of improved analytical methods, thin-layer methods and polarography the solution of streptomycin (SM) briefly reacted with aluminum amalgam at low pH were found to contain varying amounts of a certain new product, which is neither of the two known reduction products of SM., i.e., dihydro- and dihydrodeoxystreptomycin (DS and DDS, respectively). Although attempted isolation of this product failed because of its limited stability in solution, several characteristic reactions of this product were revealed. It is readily reducible to DDS with sodium borohydride. Though it is fairly stable only when pH of the solution is between 2 and 3 at room temperature, it gives a volatile compound absorbing at 271mμ, in the distillate, when distilled with steam at pH 2 to 4. This volatile compound, identified as 2-methyl-3-formylfuran, presumably originates from the reduced streptose moiety of the new reduction product of SM. This new product is probably a 2e, 2H+ reduction product of SM, and is different from DS which is also a product of 2e, 2H+ reduction at the branched formyl group (C-6) of streptose moiety of SM.
社団法人日本農芸化学会の論文