3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranose | 135824-45-2

• 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-β-D-galactopyranose
• 英文别名: [(2R,3R,4R,6R)-3,4-diacetyloxy-6-hydroxyoxan-2-yl]methyl acetate
• CAS: 135824-45-2
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: KQMOFVGDOWGPPD-DDHJBXDOSA-N

物化性质

• 沸点：
  125-131 °C(Press: 0.03 Torr)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 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：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 水 、 lithium bromide 作用下， 以 乙腈 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  AuCl3催化半缩醛活化用于立体选择性合成2-脱氧海藻糖衍生物

  摘要：

  描述了一种使用半缩醛糖基供体和受体通过 AuCl 3催化的脱水糖基化直接获得 1,1-α,α'-连接的 2-脱氧海藻糖类似物的实用、催化和高度立体选择性的新方法。该方法依赖于在其他反应性较低的半缩醛存在下，三苯甲基化 2-脱氧半缩醛的化学选择性布朗斯台德酸型活化。

  DOI：

  10.1021/acs.orglett.2c02530

文献信息

• Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing
  作者：Estelle Durantie、Christoph Bucher、Ryan Gilmour

  DOI：10.1002/chem.201200468

  日期：2012.6.25

  Validation of the 2‐fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2‐fluoro‐3,4,6‐tri‐O‐benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization

  提出了将2-氟取代基作为控制化学糖基化反应的惰性指导基团的验证方法。一项分子编辑研究表明，通过使用2-氟-3,4,6-三-O-苄基吡喃葡萄糖基三氯乙酰亚氨酸酯（TCA）支架，糖基化过程中非对映异构控制的异常水平是2 R，3 S，4的结果S立体三合会。这项研究还表明，C4的差向异构作用会导致β选择性大大提高（高达β/α300：1）。
• [EN] MULTIVALENT LIGAND CLUSTERS FOR TARGETED DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] AGRÉGATS DE LIGANDS MULTIVALENTS POUR L'ADMINISTRATION CIBLÉE D'AGENTS THÉRAPEUTIQUES
  申请人：MITOTHERAPEUTIX LLC

  公开号：WO2020191183A1

  公开（公告）日：2020-09-24

  Targeting ligand clusters, and methods of preparing same, are described. A targeting ligand cluster may include first linkers attached to phenolic hydroxyl groups of gallic acid, and one or more targeting ligands attached to each of the first linkers. The targeting ligand cluster may also include a second linker attached to a carboxylic acid of the gallic acid, and at least one of a protecting group, a phosphoramidite, or an oligonucleotide attached to the second linker.

  描述了针对配体团簇以及制备方法。一个针对配体团簇可能包括连接到没食子酸酚羟基的第一连接剂，以及连接到每个第一连接剂的一个或多个靶向配体。该针对配体团簇还可能包括连接到没食子酸羧基的第二连接剂，以及至少一种保护基团、磷酰胺酯或寡核苷酸连接到第二连接剂。
• [EN] 2'-MODIFIED NUCLEOSIDE BASED OLIGONUCLEOTIDE PRODRUGS<br/>[FR] PROMÉDICAMENTS OLIGONUCLÉOTIDIQUES À BASE DE NUCLÉOSIDES MODIFIÉS EN 2'
  申请人：[en]ALNYLAM PHARMACEUTICALS, INC.

  公开号：WO2022147223A2

  公开（公告）日：2022-07-07

  This invention relates to an oligonucleotide comprising one or more 2'-modified nucleosides, wherein the 2'-position of the nucleoside has a structure of formula (I). The invention also relates to a pharmaceutical composition comprising the oligonucleotide described herein and a method of reducing or inhibiting the expression of a target gene by administering to the subject a therapeutically effective amount of the oligonucleotide described herein. The invention also relates to a method of bioactivating an oligonucleotide comprising one or more 2'-modified nucleosides, wherein the 2'-position of the nucleoside is modified by a bio-cleavable linking group, wherein the bio-cleavable linking group comprises acetal, disulfide, carbamate, amide, sulfonamide, a biocleavable carbohydrate linker, or combinations thereof, said method comprising the step of: exposing the oligonucleotide to a physiological condition that causes the bio-cleavable linking group to be cleaved from the 2'-modified nucleoside, thereby regenerating the 2'-OH group of the nucleoside.