6-fluoro-L-6-deoxy-galactose | 447-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-fluoro-L-6-deoxy-galactose
• 英文别名: 6-fluoro-ξ-L-6-deoxy-galactopyranose；(3S,4R,5S,6R)-6-(fluoromethyl)oxane-2,3,4,5-tetrol
• CAS: 447-25-6；18961-68-7；34168-77-9；62182-12-1；62182-13-2；143616-86-8
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: SHFYXYMHVMDNPY-DHVFOXMCSA-N

物化性质

• 熔点：
  161-162°C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT, IRRITANT-HARMFUL
• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  6-fluoro-L-6-deoxy-galactose 在 氢溴酸 、 溶剂黄146 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 dibenzylphosphoryl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-L-galactopyranoside
  参考文献：
  名称：

  Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

  摘要：

  An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed. and the fluorinated sugar nucleotides have been used as probes For glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nuclceotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00139-5
• 作为产物：
  描述：

  L-galactose 在 2,4,6-三甲基吡啶 、 二乙胺基三氟化硫 、 硫酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 生成 6-fluoro-L-6-deoxy-galactose
  参考文献：
  名称：

  [EN] NOVEL SUGAR DERIVATIVES AND USES THEREOF TO PREPARE NOVEL SENOLYTIC AGENTS
  [FR] NOUVEAUX DÉRIVÉS DE SUCRE ET LEURS UTILISATIONS POUR PRÉPARER DE NOUVEAUX AGENTS SÉNOLYTIQUES

  摘要：

  Provided herein are novel sugar derivatives which are intermediates for preparing senolytic agents that selectively kill senescent cells associated with numerous pathologies and diseases, including age-related pathologies and diseases.

  公开号：

  WO2023039292A2

文献信息

• SYNTHESIS OF (6-²H)- AND 6-DEOXY-6-FLUORO-<scp>L</scp>-GALACTOSE DERIVATIVES¹
  作者：Meinolf Brackhagen、Hanna Boye、Christian Vogel

  DOI：10.1081/car-100102541

  日期：2001.2.4

  The selective oxidation of trimethylsilylated D-galactose diethyl dithioacetal using Collins reagent provided the corresponding D-galacto-hexo-dialdo dithioacetal. Successive acid hydrolysis, isopropylidenation, and cleavage of the dithioacetal group gave the 1,2;3,4-di- O-isopropylidene-L-galacto-hexodialdo-1,5-pyranose as a key intermediate for the synthesis of 6-fluoro-and 6-deutero-substituted

  使用柯林斯试剂对三甲基甲硅烷基化的D-半乳糖二乙基二硫缩醛进行选择性氧化，可提供相应的D-半乳糖-己二醛-二缩醛二硫缩醛。连续的酸水解，异亚丙基化和二硫缩醛基的裂解，得到了1,2; 3,4-二-O-异亚丙基-L-半乳糖-己二醛-1,5-吡喃糖，是合成6-氟的关键中间体-和6-氘取代的L-岩藻糖衍生物。1献给PeterKöll教授60岁生日。
• Immunogenicity Study of Globo H Analogues with Modification at the Reducing or Nonreducing End of the Tumor Antigen
  作者：Hsin-Yu Lee、Chien-Yu Chen、Tsung-I Tsai、Shiou-Ting Li、Kun-Hsien Lin、Yang-Yu Cheng、Chien-Tai Ren、Ting-Jen R. Cheng、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja508040d

  日期：2014.12.3

  these modified Globo H antigens were then conjugated with the carrier protein diphtheria toxoid cross-reactive material (CRM) 197 (DT), and combined with a glycolipid C34 as an adjuvant designed to induce a class switch to form the vaccine candidates. After Balb/c mice injection, the immune response was studied by a glycan array and the results showed that modification at the C-6 position of reducing

  基于 Globo H 的治疗性癌症疫苗已在临床试验中进行了测试，用于治疗晚期乳腺癌、卵巢癌和前列腺癌。在这项研究中，我们探索了 Globo H 类似物抗原，试图增强疫苗设计中的抗原特性。使用化学酶法合成在还原或非还原端修饰的 Globo H 类似物，然后将这些修饰的 Globo H 抗原与载体蛋白白喉类毒素交叉反应材料 (CRM) 197 (DT) 结合，并与糖脂结合C34 作为一种佐剂，旨在诱导类别转换以形成候选疫苗。Balb/c 小鼠注射后，通过聚糖阵列研究免疫反应，结果表明在 C-6 位修饰降低 Globo H 末端葡萄糖的氟、叠氮基、或苯基引发 IgG 抗体反应以特异性识别 Globo H (GH) 和 GH 相关表位、阶段特异性胚胎抗原 3 (SSEA3) (也称为 Gb5) 和阶段特异性胚胎抗原 4 (SSEA4)。然而，只有在非还原末端岩藻糖的 C-6 位置用叠氮基修饰 Globo
• Synthesis and biological activity of potential antimetabolites of L-fucose
  作者：Jesse A. May、Alan C. Sartorelli

  DOI：10.1021/jm00194a017

  日期：1979.8

  6-Substituted 6-deoxy-L-galactose (L-fucose) derivatives were synthesized as potential antimetabolites of L-fucose. The cytotoxic effects of these compounds were evaluated on P388 leukemia cells in culture. The L-fucose analogues which showed the most potent growth inhibition were the sulfonyl ester, bromo, and iodo derivatives; since these compounds were all capable of alkylation, it is conceivable

  合成6-取代的6-脱氧-L-半乳糖（L-岩藻糖）衍生物作为L-岩藻糖的潜在抗代谢物。评价了这些化合物对培养中的P388白血病细胞的细胞毒性作用。显示出最强的生长抑制作用的L-岩藻糖类似物是磺酰基酯，溴和碘衍生物。由于这些化合物都能够烷基化，因此可以认为它们的细胞毒性作用是这种性质的结果。与该解释一致，合成的试剂均未显示出对L- [3H]岩藻糖掺入糖蛋白的特异性抑制。
• Synthesis and analgesic activity of some 14.beta.-substituted analogs of morphine
  作者：Peter Osei-Gyimah、Sydney Archer

  DOI：10.1021/jm00176a011

  日期：1980.2

  prepared by the reaction of thebaine with N-bromosuccinimide and N-chlorosuccinimide, respectively. These 14 beta-substituted codeine and codeinones were O-demethylated to the corresponding morphine analogues with boron tribromide. With the exception of 14 beta-nitromorphinone, which was weak in activity, all the other 14 beta-substituted morphine derivatives were approximately equal in potency to normorphine

  用硼氢化钠处理14β-硝基可待因酮得到可待因衍生物，其在乙酸酐-乙酸溶液中用锌粉还原，得到14β-乙酰氨基可待因6-乙酸盐。从蒂巴因与硫氰酸根的反应获得14β-硫氰基可待因酮，并用氢化铝锂将其还原为14β-巯基可待因。通过蒂巴因分别与N-溴代琥珀酰亚胺和N-氯代琥珀酰亚胺反应，制备了14个β-溴-和14个-氯可待因酮。用三溴化硼将这14个β-取代的可待因和可待因酮O-去甲基化为相应的吗啡类似物。除了活性较弱的14个β-硝基吗啡酮外，
• Chemoenzymatic synthesis of the sialyl Lewis X glycan and its derivatives
  作者：David Soriano del Amo、Wei Wang、Christen Besanceney、Tianqing Zheng、Yizheng He、Brian Gerwe、Ronald D. Seidel、Peng Wu

  DOI：10.1016/j.carres.2010.03.032

  日期：2010.6

  A combination of recombinant FKP and alpha-(1 -> 3)-fucosyltransferase allows the facile synthesis of the sialyl Lewis X tetrasaccharide glycan and its derivatives in excellent yield. In this system, the universal fucosyl donor, guanidine 5'-diphosphate-beta-L-fucose (GDP-fucose), or its analogues can be generated in situ by cofactor recycling using pyruvate kinase. (C) 2010 Elsevier Ltd. All rights reserved.