Department of Chemistry, 80 St. George Str. Toronto, ON, Canada.
Carbohydr Res. 2010 Oct 13;345(15):2282-6. doi: 10.1016/j.carres.2010.08.002. Epub 2010 Aug 10.
The synthesis of methyl α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranoside and methyl α-l-rhamnopyranosyl-(1→2)-3-(glycer-2-yl-phosphate)-β-d-galactopyranoside disaccharides from the Streptococcuspneumoniae type 23F capsular polysaccharide is reported. A simple protecting group strategy was followed using commercially available monosaccharides and phosphorylating reagents. H-Phosphonate and phosphoramidite coupling chemistries were explored for introducing the phosphodiester. Hydrazine hydrate was found to be a mild and efficient deacetylating agent, which was required to avoid phosphate migration during the deprotection of the phosphodiester functionalized disaccharide.
报道了从肺炎链球菌 23F 荚膜多糖中合成甲基 α-l-鼠李吡喃糖基-(1→2)-β-d-半乳糖吡喃糖苷和甲基 α-l-鼠李吡喃糖基-(1→2)-3-(甘油-2-基-磷酸)-β-d-半乳糖吡喃糖苷二糖。采用了一种简单的保护基策略，使用商业可得的单糖和磷酸化试剂。研究了 H-膦酸酯和亚磷酰胺偶联化学，以引入磷酸二酯键。发现水合肼是一种温和且高效的脱乙酰化试剂，这是在脱保护磷酸二酯基化二糖时避免磷酸迁移所必需的。
