Sakee Uthai, Nasuk Chiradet, Grigg Ronald
Center of Excellence for Innovation in Chemistry, Department of Chemistry, Mahasarakham University, Thailand.
Carbohydr Res. 2009 Oct 12;344(15):2096-9. doi: 10.1016/j.carres.2009.06.021. Epub 2009 Jun 25.
Iodination of 1-C-(tetra-O-acetyl-beta-d-galactopyranosyl)allene affords an E/Z-mixture of 1-C-(tetra-O-acetyl-beta-d-galactopyranosyl)-2,3-diiodo-1-propene. S(N)2 displacement of the allylic iodide with primary amines affords an E/Z-mixture of allylic amines under a variety of conditions. Due to its experimental simplicity and low cost of reagents, this procedure may find wide use in the laboratory for functionalization of sugar allenes.
1-C-（四-O-乙酰基-β-D-吡喃半乳糖基）丙二烯的碘化反应生成1-C-（四-O-乙酰基-β-D-吡喃半乳糖基）-2,3-二碘-1-丙烯的E/Z混合物。在各种条件下，烯丙基碘与伯胺的S(N)2取代反应生成烯丙基胺的E/Z混合物。由于其实验操作简单且试剂成本低，该方法可能在实验室中广泛用于糖基丙二烯的官能团化。
