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The desired β anomer featured no coupling to H2″ whereas the a anomer had a coupling constant of 4 Hz.
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4 led to the decomposition of the azide prior to liberation of the anomeric center.
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2642681563
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note
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Use of benzyl bromide instead of allyl bromide as an electrophile led to decomposition under conditions necessary for reaction while Lewis acid promoted benzylation with benzyl 2,2,2-trichloroacetimidate led to reclosure to 28.
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