Ali Muhammad K S, George Jaise Mariya, Nanabala Raviteja, Antony Anitta, Muhammed K Anees, Kottuparamban Dilshad, Pokkat Junais, Arun P K, Kuni Shinooj Maniyoth, Pazhakkal Vishnunath, George Thomas, Pillai Maroor Raghavan Ambikalamajan
Molecular Radionuclidepharmacy Pvt. Ltd., Molecular Group of Companies, Ernakulam, Kerala, India.
Molecular Cyclotrons Pvt. Ltd., Molecular Group of Companies, Ernakulam, Kerala, India.
Indian J Nucl Med. 2025 May-Jun;40(3):146-151. doi: 10.4103/ijnm.ijnm_102_24. Epub 2025 Aug 7.
1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose (mannose triflate), the precursor used for the synthesis of [F] Fluorodeoxyglucose ([F] FDG) is imported from a few commercial suppliers abroad. As part of self-reliance, a reliable synthesis and characterization of mannose triflate has been developed, details of which are reported in this paper.
Synthesis of 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose (Mannose triflate) carried by Triflation of 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose with Tf2O-pyridine under argon atmosphere for 6 h. Synthesized mannose triflate is used for the production of [F] FDG using siemens explora FDG-4-automated module.
Starting from 2.6 g of 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose, mannose triflate was synthesized with an overall yield of ~ 3.0 g (~80%). The synthesis was systematically scaled up to 52 g based on the experience from the initial small size batches. The characterization of the product was done by Infra Red, Nuclear Magnetic Resonance and Mass spectroscopy. The precursor was used in the manufacture of [F] FDG using Siemens Explora synthesis module. Radiochemical yields of 55% ± 2% (decay uncorrected), radiochemical purity >96% were obtained which is comparable with the imported precursor. All the quality control parameters were within the limits as per pharmacopoeia when the in-house synthesized mannose triflate was used.
A large-scale preparation of mannose triflate is now carried out to satisfy the growing needs for FDG in positron emission tomography centers and hospitals.
用于合成[F]氟脱氧葡萄糖（[F] FDG）的前体1,3,4,6 - 四 - O - 乙酰基 - 2 - O - 三氟甲磺酰基 - β - D - 甘露吡喃糖（甘露糖三氟甲磺酸酯）从国外几家商业供应商进口。作为自力更生的一部分，已开发出可靠的甘露糖三氟甲磺酸酯合成及表征方法，本文报告其详细情况。
在氩气氛围下，用三氟甲磺酸酐 - 吡啶对1,3,4,6 - 四 - O - 乙酰基 - β - D - 甘露吡喃糖进行三氟甲磺酰化反应6小时，合成1,3,4,6 - 四 - O - 乙酰基 - 2 - O - 三氟甲磺酰基 - β - D - 甘露吡喃糖（甘露糖三氟甲磺酸酯）。合成的甘露糖三氟甲磺酸酯用于使用西门子探索者FDG - 4自动模块生产[F] FDG。
以2.6克1,3,4,6 - 四 - O - 乙酰基 - β - D - 甘露吡喃糖为起始原料，合成了约3.0克（~80%）的甘露糖三氟甲磺酸酯。基于最初小批量生产的经验，该合成方法系统地扩大到了52克。通过红外光谱、核磁共振和质谱对产物进行了表征。该前体用于使用西门子探索者合成模块制造[F] FDG。获得了55%±2%（未校正衰变）的放射化学产率，放射化学纯度>96%，与进口前体相当。当使用内部合成的甘露糖三氟甲磺酸酯时，所有质量控制参数均在药典规定的限度内。
目前正在大规模制备甘露糖三氟甲磺酸酯，以满足正电子发射断层扫描中心和医院对FDG日益增长的需求。
