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Efficient Preparation of a 1,3-Diazidocyclitol as a Versatile 2-Deoxystreptamine Precursor

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NIAID Data Ecosystem2026-03-06 收录
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https://figshare.com/articles/dataset/Efficient_Preparation_of_a_1_3_Diazidocyclitol_as_a_Versatile_2_Deoxystreptamine_Precursor/3334486
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A synthesis route toward 2-deoxystreptamine, a common structure in many of the clinically important aminoglycosides, is presented. Starting from p-benzoquinone and cyclopentadiene, 2-deoxystreptamine is synthesized with key steps involving Pd(0)-catalyzed rearrangement, a retro-Diels−Alder by flash vacuum thermolysis, and Yb(III)-directed regioselective epoxide opening. The obtained diazidocyclitol 17 is a suitable 2-deoxystreptamine precursor, conveniently protected for incorporation in new aminoglycoside entities.
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2016-05-06
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