1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside | 85951-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside
• 英文别名: (3aR,5R,6S,6aR)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol；1,2-O-iso-propylidene-5-O-tert-butyldimethylsilyl-α-D-xylofuranoside；1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-α-D-lyxofuranoside；5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose；5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylofuranoside；5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylofuranose；alpha-D-Xylofuranose, 1,2-O-isopropylidene-5-(t-butyldimethylsilyl)-；(3aR,5R,6S,6aR)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 85951-12-8
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: WHHPDHGRRYXEHB-WRWGMCAJSA-N

物化性质

• 沸点：
  127-129 °C(Press: 0.002 Torr)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 aluminum oxide 、 ammonium cerium (IV) nitrate 作用下， 以 乙醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 1,2-O-isopropylidene-5-O-(methoxycarbonyl)-α-D-xylofuranose
  参考文献：
  名称：

  Alkyloxycarbonyl group migration in furanosides

  摘要：

  A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C-13 labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.117
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 咪唑 、 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

  摘要：

  Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring a-glucosidase inhibitor, salacinol (la), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their a-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to la, and proved the importance of cooperative role of the polar substituents for the a-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.040

文献信息

• Mechanistic Insight into Aerobic Alcohol Oxidation Using NO_<i>x</i>–Nitroxide Catalysis Based on Catalyst Structure–Activity Relationships
  作者：Masatoshi Shibuya、Shota Nagasawa、Yuji Osada、Yoshiharu Iwabuchi

  DOI：10.1021/jo501862k

  日期：2014.11.7

  The mechanism of an NOx-assisted, nitroxide(nitroxyl radical)-catalyzed aerobic oxidation of alcohols was investigated using a set of sterically and electronically modified nitroxides (i.e., TEMPO, AZADO (1), 5-F-AZADO (2), 5,7-DiF-AZADO (3), 5-MeO-AZADO (4), 5,7-DiMeO-AZADO (5), oxa-AZADO (6), TsN-AZADO (7), and DiAZADO (8)). The motivation for the present study stemmed from our previous observation

  的NO的机制X -assisted，硝基氧（氮氧自由基）催化使用一组空间上和电子改性氮氧自由基（醇的有氧氧化进行了研究，即，TEMPO，AZADO（1），5-F-AZADO（2）， 5,7-DiF-AZADO（3），5-MeO-AZADO（4），5,7-DiMeO-AZADO（5），oxa-AZADO（6），TsN-AZADO（7）和DiAZADO（8） ）。用于本研究的动机来自我们先前观察梗，在从上氮杂金刚烷核硝酰自由基部分的远程位置引入一个F原子的有效地提高在典型的NO的催化活性X介导的有氧氧化条件。氮杂金刚烷-N-氧基-[AZADO（1）-，5-F-AZADO（2）-和5,7-DiF-AZADO（3）]催化的需氧氧化的动力学曲线进行了仔细研究，发现与5-F-AZADO（2）和5,7-DiF-AZADO（3）相比，AZADO（1）表现出较高的初始反应速率；然而，AZADO催化的氧化反应
• Selective Cleavage of Methoxy Protecting Groups in Carbohydrates
  作者：Alicia Boto、Dácil Hernández、Rosendo Hernández、Ernesto Suárez

  DOI：10.1021/jo052313o

  日期：2006.3.1

  The selective cleavage of methoxy protecting groups next to hydroxy groups is achieved using a radical hydrogen abstraction reaction as the key step. Under the reaction conditions, the hydroxy group generates an alkoxyl radical that reacts with the sterically accessible adjacent methoxy group, which is transformed into an acetal. In the second step, the acetals are hydrolyzed to give alcohols or diols

  使用自由基氢提取反应作为关键步骤，可以实现羟基旁边的甲氧基保护基的选择性裂解。在反应条件下，羟基产生烷氧基，该烷氧基与空间可及的相邻甲氧基反应，转化为乙缩醛。在第二步中，将乙缩醛水解得到醇或二醇。还开发了一种一锅取氢的水解程序。通常可获得良好的收率，并且该方法的温和条件与不同的官能团和敏感的底物（例如碳水化合物）相容。
• An Efficient Synthesis of Enantiopure 1-Alkoxy-1,2-propadienes from Propargyl Bromide
  作者：Patrick Rochet、Jean-Michel Vatèle、Jacques Goré

  DOI：10.1055/s-1994-25577

  日期：——

  A number of enantiopure functionalized alcohols have been O-allenylated by reaction of their corresponding sodium alcoholates with propargyl bromide followed by t-BuOK catalyzed isomerization of the resulting propargyl ethers, in good overall yields.

  一系列对映纯功能化醇通过其相应钠醇盐与丙炔溴化物反应后，再经过t-BuOK催化的异构化反应，对得到的丙炔醚进行O-烯丙基化，获得了良好的总体产率。
• An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks
  作者：Sushil K Maurya、Rohit Rana

  DOI：10.3762/bjoc.13.110

  日期：——

  An efficient, eco-compatible diversity-oriented synthesis (DOS) approach for the generation of library of sugar embedded macrocyclic compounds with various ring size containing 1,2,3-triazole has been developed. This concise strategy involves the iterative use of readily available sugar-derived alkyne/azide-alkene building blocks coupled through copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction

  已经开发出一种有效的，生态相容的，面向多样性的合成（DOS）方法，用于生成包含各种环大小的含1,2,3-三唑的糖嵌入大环化合物的文库。这种简洁的策略涉及通过铜催化的叠氮化物-炔烃环加成（CuAAC）反应偶联使用容易获得的糖衍生的炔烃/叠氮化物-烯烃构件，然后使用更绿色的反应条件配对线性环加合物。生态相容性，温和的反应条件，较绿色的溶剂，易于纯化的方法以及避免危害和有毒溶剂的使用是该方案进入这一重要结构类别的优势。
• [EN] INHIBITORS OF NUCLEOSIDE PHOSPHORYLASES AND NUCLEOSIDASES<br/>[FR] INHIBITEURS DES PHOSPHORYLASES DE NUCLEOSIDE ET DES NUCLEOSIDASES
  申请人：EINSTEIN COLL MED

  公开号：WO2004018496A1

  公开（公告）日：2004-03-04

  The present invention relates to compounds of the general formula (I) which are inhibitors of purine muclioside phosphorylases (PNP), purine phosphoribosyltransferases (PPRT), 5'-methylthioadenosine phosphorylases (MTAP), 5'-methylthioadenosine mucliosidases (MTAN) and/or nucleoside hydrolases (NH). The invention also relates to the use of these compounds in the treatment of diseases and infections including cancer, bacterial infections, protozoal infections, and T-cell mediated disease and to pharmaceutical compositions containing the compounds.

  本发明涉及一般式(I)的化合物，这些化合物是嘌呤核苷酸磷酸化酶（PNP），嘌呤磷酸核糖基转移酶（PPRT），5'-甲硫腺苷磷酸酶（MTAP），5'-甲硫腺苷核苷酸酶（MTAN）和/或核苷酸水解酶（NH）的抑制剂。本发明还涉及这些化合物在治疗疾病和感染，包括癌症、细菌感染、原虫感染和T细胞介导的疾病中的用途，以及含有这些化合物的药物组合物。