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Synthesis of methyl 4,6-O-benzylidene-2,3-dideoxy-2-(4-morpholinyl)-3-thio-α-d-glucopyranoside 16. Reaction conditions: (i) bis(2-bromoetyl) ether, MeCN, K2CO3, 80 °C, 20 h, 47%; (ii) MsCl, pyridine, r.t., 4 h, 73%; (iii) NaOAc, 2-methoxyethanol, 115 °C, 72 h, 46%; (iv) MsCl, pyridine, 4 h, r.t. 68%; (v) KSAc, DMF, 24 h, 100 °C, 70%; and (vi) LiAlH4, THF, 0 °C to r.t., 76%.
