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A Facile and Practical Synthesis of Peracylated 4-Thio-d-ribofuranoses from d-Glucose

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posted on 21.03.2008, 00:00 by Zhi-Hua Sun, Bing Wang
A practical synthesis of a peracylated 4-thio-d-ribofuranose 14 starting from inexpensive d-glucose is described. The C2−C6 portion of d-glucose was utilized, in which sulfur was introduced to C5 in two consecutive displacement reactions with net retention of configuration under mild conditions.