3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl bromide | 801291-55-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl bromide
• 英文别名: [(2R,3R,4S,5S,6R)-3,4-diacetyloxy-6-bromo-5-fluorooxan-2-yl]methyl acetate
• CAS: 801291-55-4
• 化学式: C₁₂H₁₆BrFO₇
• 分子量: 371.157
• InChiKey: HXCROXNKTXVIKX-ROHXPCBUSA-N

物化性质

• 沸点：
  385.0±42.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl bromide 在 silver carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以98%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranose
  参考文献：
  名称：

  The Chameleon of Retaining Glycoside Hydrolases and Retaining Glycosyl Transferases: The Catalytic Nucleophile

  摘要：

  This paper addresses the existence and role of a catalytic nucleophile in retaining glycoside hydrolases and retaining glycosyl transferases. Although the former has now been established beyond doubt, such is not the case with the latter. We report reliable procedures for the synthesis of various 2-deoxy-2-fluoro glycosyl nucleoside diphosphates, useful donor analogues for the study of the mechanism of action of retaining glycosyl transferases.

  DOI：

  10.1007/s007060200027
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以94%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  Synthesis of Fluorosugar Reagents for the Construction of Well-Defined Fluoroglycoproteins

  摘要：

  2-Deoxy-2-fluoroglycosyl iodides are privileged glycosyl donors for the stereoselective preparation of 1-Nu-beta-fluorosugars, which are useful reagents for chemical site-selective protein glycosylation. Ready access to such beta-fluorosugars enables the mild and efficient construction of well-defined fluoroglycoproteins.

  DOI：

  10.1021/acs.orglett.5b01259

文献信息

• Oxidative Activation of C–S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides
  作者：Annabel Kitowski、Ester Jiménez-Moreno、Míriam Salvadó、Jordi Mestre、Sergio Castillón、Gonzalo Jiménez-Osés、Omar Boutureira、Gonçalo J. L. Bernardes

  DOI：10.1021/acs.orglett.7b02886

  日期：2017.10.6

  method for the selective activation of thioglycosides that uses the N+-thiophilic reagent O-mesitylenesulfonylhydroxylamine (MSH) as a promoter is presented. The reaction proceeds via anomeric mesitylensulfonate intermediates, which could be isolated and fully characterized by placing a fluorine atom at the C2 position. In the presence of a soft Lewis acid, glycosylation reaction proceeds at ambient temperature

  提出了一种选择性活化硫糖苷的方法，该方法使用N +-亲硫试剂O-均三甲苯磺酰基羟胺（MSH）作为促进剂。该反应通过异戊基均磺酸磺酸盐中间体进行，该中间体可以被分离并且可以通过将氟原子置于C 2位来充分表征。在软路易斯酸的存在下，糖基化反应在环境温度下以良好的产率进行。进一步证明，在S-苯基供体的存在下可以正交活化S-乙基，从而可以设计顺序糖基化策略。
• Conjugates of 2-fluoro-2-deoxy-glucose and their uses as anti cancer agents
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1881000A1

  公开（公告）日：2008-01-23

  The present invention relates to compounds of general formula (I): wherein: - R1, R2 and R3 mean, independently from the others, an hydrogen atom or an optionally substituted lower alkyl, a (C1-C7)acyl group or a benzyl, - R4 is an optionally substituted and/or interrupted hydrocarbon linker, - X and Y are selected independently from each other from the group consisting of -NH-, -NR'-, -CO-, -NH(CO)-, -NH(CO)NH-, -NR'(CO)-, -O(CO)NH-, -O(CO)NR'-, -(CO)NH-, -(CO)NR'-, -NH(CO)(R")NH(CO)-, -(CO)NH(R"(CO)NH-, -O-, -(CO)O-, -NH(CO)O-, -SC(O)NH-, -NHSO2-, -NR'SO2- and -O(CO)- and preferably are different one from the other, with R' being an optionally substituted lower alkyl group, and R" being a (C1-C3) alkylene, - Z moiety represents an anti-neoplasic agent, - n means 0 or 1, - and the pharmaceutically acceptable salts thereof. It relates also to the use of such compounds as anti cancer agents.

  本发明涉及一般式（I）的化合物：其中：- R1、R2和R3分别独立地表示氢原子或可选择取代的较低烷基，（C1-C7）酰基团或苄基，- R4是可选择取代和/或中断的碳氢链，- X和Y分别独立地从-NH-，-NR'-，-CO-，-NH（CO）-，-NH（CO）NH-，-NR'（CO）-，-O（CO）NH-，-O（CO）NR'-，-（CO）NH-，-（CO）NR'-，-NH（CO）（R"）NH（CO）-，-（CO）NH（R"（CO）NH-，-O-，-（CO）O-，-NH（CO）O-，-SC（O）NH-，-NHSO2-，-NR'SO2-和-O（CO）-中选择，并且最好彼此不同，其中R'是可选择取代的较低烷基团，R"是（C1-C3）烷基，- Z基团代表抗肿瘤剂，- n表示0或1，- 及其药用盐。还涉及将这些化合物用作抗癌剂。
• Synthesis of a library of 2-fluoro-2-deoxy-derivatives of the trimannoside methyl α-D-Man-(1 → 3)-[α-D-Man-(1 → 6)]-α-D-Man and the dimannosides methyl α-D-Man-(1 → 3)-α-D-Man and methyl α-D-Man-(1 → 6)-α-D-Man
  作者：Angela Simona Infantino、Dennis Bengtsson、Stefan Oscarson

  DOI：10.1016/j.carres.2022.108515

  日期：2022.2

  十六种化合物的文库，1-16，包含 N-聚糖核心三甘露糖苷 α-D-Man-(1 → 3) 的所有（单-、二-和三-）2-氟-2-脱氧衍生物-[α-D-Man-(1 → 6)]-D-Man，包括相应的 2-氟-2-脱氧二糖部分结构和非氟化母体化合物，已合成为它们的 α-甲基糖苷用作基于 19F NMR 的凝集素-碳水化合物相互作用研究的工具。构建了两个甲基 2-氟-2-脱氧甘露糖苷受体 21 (3-OH) 和 22 (6-OH)，并与相应的非氟化甘露糖受体 24 (6-OH) 和 25 结合使用(3-OH)、2-氟-2-脱氧甘露糖基溴供体18和非氟化溴供体23有效地提供目标二糖和三糖（二糖，2-3步，总产率47-66%；三糖，4 步，25-40% 总产率）。
• [EN] PYRAN DERIVATIVES AS CCR3 MODULATORS<br/>[FR] DÉRIVÉS DE PYRANE EN TANT QUE MODULATEURS DU CCR3
  申请人：NYCOMED GMBH

  公开号：WO2010069979A1

  公开（公告）日：2010-06-24

  The compounds of formula (1) wherein A, B, R1, R2 and R3 have the meanings as given in the description, the stereoisomers, as well as the salts of the stereoisomers thereof are effective CCR3 modulators.

  式（1）中A、B、R1、R2和R3具有描述中给定的含义的化合物，其立体异构体以及其立体异构体的盐是有效的CCR3调节剂。
• The synthesis of a series of modified mannotrisaccharides as probes of the enzymes involved in the early stages of mammalian complex N-glycan formation
  作者：Chris A. Tarling、Stephen G. Withers

  DOI：10.1016/j.carres.2004.08.007

  日期：2004.10

  D-mannopyranoside (8) were rapidly synthesized from unprotected methyl beta-D-mannopyranoside (12). Methyl (2-deoxy-2-fluoro-alpha-D-mannopyranosyl)-(1-->3)-[(alpha-D-mannopyranosyl)-(1--> 6)]-beta-D-mannopyranoside (7) and methyl (alpha-D-mannopyranosyl)-(1-->3)-[(2-deoxy-2-fluoro-alpha-D-mannopyranosyl)-(1--> 6)]-beta-D-mannopyranoside (9) were synthesized from the common orthogonally protected precursor

  通过两种不同的化学途径合成了一系列甘露三糖，作为哺乳动物复杂N-聚糖形成早期所涉及的酶的探针。甲基（α-D-甘露糖吡喃糖基）-（1-> 3）-[（（α-D-甘露糖吡喃糖基）-（1-> 6）]-β-D-甘露糖吡喃糖苷（6）和甲基（2-脱氧-2-氟代-α-D-甘露吡喃糖基）-（1-> 3）-[（2-脱氧-2-氟代-α-D-甘露聚糖基吡喃糖基）-（1-> 6）]-β-D -甘露糖吡喃糖苷（8）是由未保护的甲基β-D-甘露糖吡喃糖苷（12）快速合成的。甲基（2-脱氧-2-氟-α-D-甘露吡喃糖基）-（1-> 3）-[（（α-D-甘露吡喃糖基）-（1-> 6）]-β-D-甘露吡喃糖苷（7 ）和甲基（α-D-甘露吡喃糖基）-（1-> 3）-[（（2-脱氧-2-氟-α-D-甘露吡喃糖基）-（1-> 6）]-β-D-甘露吡喃糖苷（9）由常见的正交保护的甲基2-O-乙酰基-4合成，6-O-亚苄基-β-D-甘