Luxen A, Satyamurthy N, Bida G T, Barrio J R
Int J Rad Appl Instrum A. 1986;37(5):409-13. doi: 10.1016/0883-2889(86)90097-3.
The reaction of methyl 4,6-O-benzylidene-3-O-benzyl-2-O-trifluoromethanesulfonyl-beta-D- glucopyranoside in acetonitrile at 75 degrees C for 30 min with [18F]tetra-n-butylammonium fluoride, followed by silica gel column chromatographic purification, gave the corresponding [18F]methyl 4,6-O-benzylidene-3-O-benzyl-2-fluoro-beta-D-mannopyranoside with complete regio- and stereoselectivity (42% radiochemical yield). Hydrolysis of the radiolabeled fluoromannopyranoside intermediate with either 6 N HCl or 50% methanesulfonic acid for 30 min at 120 degrees C, followed by purification by column chromatography (ion retardation resin and neutral alumina), gave pure [18F]2-deoxy-2-fluoro-D-mannose ([18F]2-FDM) with an overall radiochemical yield (from [18F]fluoride ion) of 34%. Extension of this methodology to the no carrier added (nca) synthesis under phase transfer conditions (Kryptofix 222/K 18F/acetonitrile) gave nca [18F]2-FDM in a radiochemical yield of 75%. Purity and identity of the fluorinated products were confirmed by 1H and 19F NMR spectroscopy. The synthetic procedure described here permits for the first time the routine preparation of large amounts of [18F]2-FDM for tomographic studies.
4,6-O-亚苄基-3-O-苄基-2-O-三氟甲磺酰基-β-D-吡喃葡萄糖苷甲酯在乙腈中于75℃与[18F]四丁基氟化铵反应30分钟，然后经硅胶柱色谱纯化，得到相应的具有完全区域和立体选择性的[18F]4,6-O-亚苄基-3-O-苄基-2-氟-β-D-甘露吡喃糖苷（放射化学产率42%）。用6 N盐酸或50%甲磺酸在120℃对放射性标记的氟代甘露吡喃糖苷中间体水解30分钟，然后通过柱色谱（离子阻滞树脂和中性氧化铝）纯化，得到纯的[18F]2-脱氧-2-氟-D-甘露糖（[18F]2-FDM），总放射化学产率（从[18F]氟离子算起）为34%。将此方法扩展到相转移条件（穴醚222/K [18F]/乙腈）下的无载体添加（nca）合成，得到放射化学产率为75%的nca [18F]2-FDM。氟化产物的纯度和结构通过1H和19F NMR光谱得到确认。本文所述的合成方法首次允许常规制备大量用于断层扫描研究的[18F]2-FDM。
