2-O-methanesulfonyl-β-D-mannose | 221252-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-methanesulfonyl-β-D-mannose
• 英文别名: [(2R,3S,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl] methanesulfonate
• CAS: 221252-44-4
• 化学式: C₇H₁₄O₈S
• 分子量: 258.249
• InChiKey: CZEHQLCMHQVRBL-ULQPCXBYSA-N

物化性质

• 沸点：
  595.9±50.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-O-methanesulfonyl-β-D-mannose 在 四乙基氟化铵水合物 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以500 mg的产率得到β-D-glucosyl fluoride
  参考文献：
  名称：

  Synthesis of 1-[18F]fluorodeoxyglucose: an unexpected rearrangement in the reaction of 2-O-methanesulfonyl-β-D-mannopyranose with [18f] fluoride

  摘要：

  2-O-Methanesulfonyl-beta-D-mannose was reacted with kryptofix/K2CO3/[F-18]fluoride in CH3CN/THF (9:1) at 60 degrees C. Unexpectedly, a mixture of 1 alpha- and 1 beta-glucopyranosyl [F-18]fluoride (4 and 5, respectively) was obtained in 50% radiochemical yield (EOB); 2-[F-18]FDG was not detected. Modification of temperature, solvent or pH did riot result in the formation of 2-[F-18]FDG. Uptake of radioactivity in heart and brain of mice was significantly lower for 4 and 5 than for 2-[F-18]FDG, although 5 seems to pass the blood-brain barrier. Uptake in bone was more pronounced for 4 than for 5 and negligible for 2-[F-18]FDG.

  DOI：

  10.1002/(sici)1099-1344(199902)42:2<147::aid-jlcr176>3.0.co;2-e
• 作为产物：
  描述：

  1,3,4,6-四-氧-乙酰-Β-D-吡啶甘露糖 在 吡啶 、 盐酸 作用下， 反应 2.5h， 生成 2-O-methanesulfonyl-β-D-mannose
  参考文献：
  名称：

  Synthesis of 1-[18F]fluorodeoxyglucose: an unexpected rearrangement in the reaction of 2-O-methanesulfonyl-β-D-mannopyranose with [18f] fluoride

  摘要：

  2-O-Methanesulfonyl-beta-D-mannose was reacted with kryptofix/K2CO3/[F-18]fluoride in CH3CN/THF (9:1) at 60 degrees C. Unexpectedly, a mixture of 1 alpha- and 1 beta-glucopyranosyl [F-18]fluoride (4 and 5, respectively) was obtained in 50% radiochemical yield (EOB); 2-[F-18]FDG was not detected. Modification of temperature, solvent or pH did riot result in the formation of 2-[F-18]FDG. Uptake of radioactivity in heart and brain of mice was significantly lower for 4 and 5 than for 2-[F-18]FDG, although 5 seems to pass the blood-brain barrier. Uptake in bone was more pronounced for 4 than for 5 and negligible for 2-[F-18]FDG.

  DOI：

  10.1002/(sici)1099-1344(199902)42:2<147::aid-jlcr176>3.0.co;2-e

文献信息

• Groot, T. de; Bormans, G.; Mortelmans, L., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 68 - 69
  作者：Groot, T. de、Bormans, G.、Mortelmans, L.、Verbruggen, A.

  DOI：——

  日期：——
• Synthesis of 1-[18F]fluorodeoxyglucose: an unexpected rearrangement in the reaction of 2-O-methanesulfonyl-β-D-mannopyranose with [18f] fluoride
  作者：Tjibbe de Groot、Guy Bormans、Roger Busson、Luc Mortelmans、Alfons Verbruggen

  DOI：10.1002/(sici)1099-1344(199902)42:2<147::aid-jlcr176>3.0.co;2-e

  日期：1999.2

  2-O-Methanesulfonyl-beta-D-mannose was reacted with kryptofix/K2CO3/[F-18]fluoride in CH3CN/THF (9:1) at 60 degrees C. Unexpectedly, a mixture of 1 alpha- and 1 beta-glucopyranosyl [F-18]fluoride (4 and 5, respectively) was obtained in 50% radiochemical yield (EOB); 2-[F-18]FDG was not detected. Modification of temperature, solvent or pH did riot result in the formation of 2-[F-18]FDG. Uptake of radioactivity in heart and brain of mice was significantly lower for 4 and 5 than for 2-[F-18]FDG, although 5 seems to pass the blood-brain barrier. Uptake in bone was more pronounced for 4 than for 5 and negligible for 2-[F-18]FDG.