1,2:5,6-di-O-isopropylidene-α-D-threo-D-glycero-3-hexofuranosulose | 26623-13-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-α-D-threo-D-glycero-3-hexofuranosulose
• 英文别名: 1,2:5,6-di-O-isopropylidene-β-L-lyxo-hexofuranos-3-ulose；1,2:5,6-Di-O-isopropylidene-α-D-xylohexofuranos-3-ulose；(3aR,5S,6aS)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[2,3-d][1,3]dioxol-6(3aH)-one；(3aR,5R,6aS)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[2,3-d][1,3]dioxol-6(5H)-one；O¹,O²;O⁵,O⁶-Diisopropyliden-α-D-xylo-3-hexofuranosulose；1,2:5,6-Di-O-isopropyliden-α-D-xylo-hexos-3-ulose；(3aR,5S,6aS)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-one
• CAS: 26623-13-2
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: QSRFRZJIRAOQSJ-XCWAXFADSA-N

物化性质

• 沸点：
  331.8±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-threo-D-glycero-3-hexofuranosulose 在 titanium(IV) isopropylate 、 lithium aluminium tetrahydride 、 氨 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 1,2,5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-glucofuranoside
  参考文献：
  名称：

  Stereoselective synthesis of α-aminonitriles at non-anomeric positions of monosaccharides

  摘要：

  alpha-Aminonitriles have been stereoselectively introduced at non-anomeric positions of monosaccharides, in which the carbon C-alpha is one of the atoms of the sugar ring. Target compounds were prepared from various ulose derivatives and amines using titanium(IV) isopropoxide as a mild and effective Lewis acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01090-x
• 作为产物：
  描述：

  双丙酮葡萄糖 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到1,2:5,6-di-O-isopropylidene-α-D-threo-D-glycero-3-hexofuranosulose
  参考文献：
  名称：

  含稀有单糖的同多价和杂多价糖代谢的多组分方法。

  摘要：

  我们应用了多组分方法来访问包含与异亚丙基保护的d-果糖，l-山梨糖，d-半乳糖和d-阿洛糖有关的醛，胺和异氰化物组分的密集功能化的均价和杂多价糖模拟物的库。获得的Passerini产品收率非常高（高达78％）和非对映异构体选择性很高（高达98：2）。通过Ugi反应获得了三种类型的产物。连同“经典的”四组分产物一起，分离出α-酰基氨基酰胺，三组分α-氨基酰胺和四组分α-氨基酰胺。亚胺酸酯中间体的结构合理化了多种途径，主要受胺成分的影响。

  DOI：

  10.1021/acs.joc.9b03401

文献信息

• [EN] PRMT5 INHIBITORS<br/>[FR] INHIBITEURS DE PRMT5
  申请人：MERCK SHARP & DOHME

  公开号：WO2020033288A1

  公开（公告）日：2020-02-13

  The present invention provides a compound of Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are PRMT5 inhibitors. Also provided are methods of making compounds of Formula I, pharmaceutical compositions comprising compounds of Formula I, and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.

  本发明提供了一种式(I)的化合物及其药用可接受的盐、酯和前药，这些化合物是PRMT5抑制剂。还提供了制备式I化合物的方法，包括含有式I化合物的药物组合物，以及使用这些化合物治疗癌症、镰状细胞贫血和遗传性胎儿血红蛋白持续性（HPFH）突变的方法。
• Unprecedented 3- O -methyl-3- C -trifluoromethyl- d -ribono- (and l -lyxono)-γ-lactones synthesized by nucleophilic trifluoromethylation of d -hexose-derived cyclic ketones
  作者：Siwar Ghannay、Jihed Brahmi、Kaïss Aouadi、Moncef Msadek、Jean-Pierre Praly

  DOI：10.1016/j.jfluchem.2016.05.002

  日期：2016.6

  d-ribono-(and l-lyxono)-γ-lactones have been prepared from protected d-hexoses (gluco, galacto) by multi-step routes from d-glucose. The synthetic strategy includes the following steps: regioselective oxidation, nucleophilic trifluoromethylation with the Ruppert-Prakash reagent of 3-keto hexofuranose derivatives attacked stereoselectively from the less hindered face, protective group manipulations

  3- ø -甲基-3- Ç三氟甲基- d -ribono-（和升-lyxono）-γ-内酯已经从保护制备d -hexoses（葡萄糖，半乳糖）通过从多步途径d -葡萄糖。合成策略包括以下步骤：区域选择性氧化，3-酮基六呋喃糖衍生物的Ruppert-Prakash试剂的Ruppert-Prakash试剂进行亲核三氟甲基化，从较少受阻的面部进行立体选择性攻击，保护基操作和半缩醛羟基的区域选择性氧化。两种相关的d-核糖内酯的碱催化水解得到3 - O -Me-3- C-CF 3 - d -ribonic酸。
• Synthetic Studies of Amphotericin B. III. An Enantiospecific Synthesis of the C-1–C-19 Segment of the Amphotericin B Aglycon
  作者：Mitsuhiro Kinoshita、Masato Taniguchi、Masahiko Morioka、Hitoshi Takami、Yasuhiro Mizusawa

  DOI：10.1246/bcsj.61.2147

  日期：1988.6

  ethoxy)methyl]-1,3,5,8,9,11-dodecanehexol (2) and (3S,4R,5S)-4-[(t-butyldimethylsilyloxy)methyl]-3,5-O-isopropylidene-1,1-bis(methylthio)-1-trimethylstannyl-6-heptene-3,5-diol (36). The C-13–C-19 segment 36 was enantiospecifically synthesized from 1,2:5,6-di-O-isopropylidene-α-D-thero-D-glycero-3-hexofuranosulose (7) via (2S,4R,5S)-5,6-epoxy-3-[(t-butyldimethylsilyloxy)methyl]-1-hexen-3-ol (6a) in

  标题化合物，(3S,4S,5S,9S,11R,12R,15R,17S)-4-[(叔丁基二甲基甲硅烷氧基)甲基]-1,3,5,9,11,12,15,17,19 -nonahydroxy-3,5:11,12:15,17-tri-O-isopropylidene-19-O-(4-methoxybenzyl)-9-O-[(2-methoxyethoxy)methyl]-7-nonadecanone (1)通过(3S,5R,8R,9R,11S)-12-iodo-3,5:8,9-di-O-isopropylidene-1-O-(4-methoxybenzyl)-11-O的偶联有效合成-[(2-甲氧基乙氧基)甲基]-1,3,5,8,9,11-十二烷己醇(2)和(3S,4R,5S)-4-[(叔丁基二甲基甲硅烷氧基)甲基]-3,5- O-isopropidene-1,1-bis(methylthio)-1-
• Unprecedented influence of remote substituents on reactivity and stereoselectivity in Cu(i)-catalysed [2 + 2] photocycloaddition. An approach towards the synthesis of tricycloclavulone
  作者：Sujit Mondal、Ram Naresh Yadav、Subrata Ghosh

  DOI：10.1039/c1ob05233k

  日期：——

  Cu(I)-catalysed [2 + 2] photocycloaddition of 1,6-dienes embedded in a furano sugar is described in connection to a synthetic approach to an abnormal marine prostanoid tricycloclavulone. An unprecedented influence of remote substituents on the reactivity and stereoselectivity of the photocycloaddition reaction has been uncovered during this investigation. While an alkene substituent inhibits cycloaddition through steric effects, a substituent having a hydroxyl or alkoxy group at the same location facilitates cycloaddition exclusively from its own side. This investigation has led to the synthesis of a functionalised 5,4-fused core unit of tricycloclavulone.

  本研究介绍了 Cu(I)-Catalysed [2 + 2] photocycloaddition of 1,6-dienes embedded in a furano sugar（呋喃糖内嵌的 1,6-二烯的光环加成反应）与异常海洋前列腺素三环黄酮的合成方法。在这项研究中，发现了偏远取代基对光环加成反应的反应性和立体选择性的前所未有的影响。烯基取代基通过立体效应抑制环化反应，而在同一位置具有羟基或烷氧基的取代基则完全从其自身一侧促进环化反应。通过这项研究，我们合成了三环黄酮的功能化 5,4-融合核心单元。
• Ortho ester Claisen rearrangements of three 3-C-(hydroxymethyl)methylene derivatives of hexofuranose: stereoselective introduction of a quaternary center on C-3 of D-ribo-, L-lyxo-, and D-arabino-hexofuranoses
  作者：Kinichi Tadano、Yoko Idogaki、Hirohiko Yamada、Tetsuo Suami

  DOI：10.1021/jo00383a005

  日期：1987.4