1-(2-(trimethylsilyl)ethyl)-2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-O-isopropylidene-β-D-glucopyranoside | 1326775-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-(2-(trimethylsilyl)ethyl)-2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: 2-trimethylsilylethyl 2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-benzylidene-β-D-glucopyranoside；2-[[(4aR,6R,7R,8S,8aR)-8-(ethoxymethoxy)-7-fluoro-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]ethyl-trimethylsilane
• CAS: 1326775-51-2
• 化学式: C₁₇H₃₃FO₆Si
• 分子量: 380.529
• InChiKey: XNFKXPNYQGICGA-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-(trimethylsilyl)ethyl)-2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-O-isopropylidene-β-D-glucopyranoside 在 三氟乙酸 作用下， 反应 0.25h， 生成 2-脱氧-2-氟-beta-D-吡喃葡萄糖 、 2-脱氧-2-氟-d-赖氨酸
  参考文献：
  名称：

  METHOD FOR PRODUCING 18F-LABELED COMPOUND AND HIGH MOLECULAR COMPOUND TO BE USED IN THE METHOD

  摘要：

  本发明的目的在于解决传统的18F-标记化合物生产方法的问题，即液相合成方法中化合物的纯化问题和固相合成方法中由于反应性降低导致产率不足的问题。提供了一种生产18F-标记化合物的方法，包括：使含有待标记前体化合物的残基和分子中的相转移催化剂残基的高分子化合物与18F-反应；并从高分子化合物中去除18F-标记化合物。

  公开号：

  US20120329968A1
• 作为产物：
  描述：

  (2-(trimethylsilyl)ethyl) 3-O-ethoxymethyl-4,6-O-isopropylidene-2-O-(1,1,2,2-tetrafluoro-2-(6-carboxy-1,1,2,2-tetrafluoro-4-iodohexa-3-enyloxy)ethanesulfonyl)-β-D-mannopyranoside 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 三氟乙酸烯丙酯 、 palladium on activated charcoal 、 C₂₄H₃₅NO₇ 、 氢气 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 30.58h， 生成 1-(2-(trimethylsilyl)ethyl)-2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-O-isopropylidene-β-D-glucopyranoside 、 2-(trimethylsilyl)ethyl 2-deoxy-3-O-ethoxymethyl-4,6-O-isopropylidene-D-arabino-hex-1-enopyranoside
  参考文献：
  名称：

  Solid-supported reagents composed of a copolymer possessing 2- O -sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose

  摘要：

  We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the pi-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel (R) resins. TentaGel (R) enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.068

文献信息

• METHOD FOR PRODUCING 18F-LABELED COMPOUND AND HIGH MOLECULAR COMPOUND TO BE USED IN THE METHOD
  申请人：Takahashi Takashi

  公开号：US20120329968A1

  公开（公告）日：2012-12-27

  The present invention aims at solving the problems of conventional methods for producing an 18 F-labeled compound, that is, the problem of purification of a compound in a liquid phase synthesis method and the problem of an insufficient yield due to the reduction of reactivity in a solid phase synthesis method. There is provided a method for producing an 18 F-labeled compound including: allowing a high molecular compound containing a residue of a precursor compound to be labeled and a residue of a phase transfer catalyst in the molecule thereof to react with 18 F − ; and removing the 18 F-labeled compound from the high molecular compound.

  本发明的目的在于解决传统的18F-标记化合物生产方法的问题，即液相合成方法中化合物的纯化问题和固相合成方法中由于反应性降低导致产率不足的问题。提供了一种生产18F-标记化合物的方法，包括：使含有待标记前体化合物的残基和分子中的相转移催化剂残基的高分子化合物与18F-反应；并从高分子化合物中去除18F-标记化合物。
• Solid-supported reagents composed of a copolymer possessing 2- O -sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose
  作者：Ryota Takeuchi、Yuki Sakai、Hiroshi Tanaka、Takashi Takahashi

  DOI：10.1016/j.bmcl.2015.10.068

  日期：2015.12

  We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the pi-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel (R) resins. TentaGel (R) enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration. (C) 2015 Elsevier Ltd. All rights reserved.