5-O-triphenylmethyl-L-arabinofuranose | 55726-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-O-triphenylmethyl-L-arabinofuranose
• 英文别名: 5-O-trityl-L-arabinofuranose；5-O-trityl-L-arabinose；(3R,4R,5S)-5-(trityloxymethyl)oxolane-2,3,4-triol
• CAS: 55726-00-6；72521-12-1；72521-13-2；72521-20-1；72521-21-2；72521-22-3；131285-09-1；131285-24-0
• 化学式: C₂₄H₂₄O₅
• 分子量: 392.452
• InChiKey: ZAZZFZLLPGMINF-JYEDNEFCSA-N

物化性质

• 沸点：
  565.5±50.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-triphenylmethyl-L-arabinofuranose 在 吡啶 、 4-二甲氨基吡啶 、 溴 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 (2R,3S,4S)-3-hydroxy-2-(phenoxythiocarbonyl)oxy-5-trityloxy-4-pentanolide
  参考文献：
  名称：

  使用苏式选择性羟醛缩合作为关键反应，从L-阿拉伯糖合成旋光性寡聚体型木脂素。

  摘要：

  由L-阿拉伯糖与胡椒醛制备的（3R，4S）-3-羟基-5-三苯甲氧基-4-戊醇的苏式选择性羟醛缩合反应用于木脂素的橄榄石型立体选择性合成（2R ，3R，4R）-4-苄基-4-羟基-3-羟基甲基-2-（3,4-亚甲基二氧苯基）四氢呋喃。

  DOI：

  10.1271/bbb.64.2320
• 作为产物：
  描述：

  L-阿拉伯糖 、 三苯基氯甲烷 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 72.0h， 以54%的产率得到5-O-triphenylmethyl-L-arabinofuranose
  参考文献：
  名称：

  Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation

  摘要：

  Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl L-tartrate and/or L-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group via [3,3]-sigmatropic rearrangements, a Wittig olefination for the instalment of the carbon backbone and the acid-promoted building-up of a tetrahydrofuran framework. Evaluation for in vitro antiproliferative/cytotoxic activity with a panel of human tumour cell lines using a MTT assay revealed for some compounds of our strategy noteworthy activity. Compound 1 center dot HCl (IC50: 0. 41-2.35 mu M), its antipode ent-1 center dot HCl (IC50: 4.07-5.69 mu M) and also stereoisomer 4 center dot HCl (IC50: 4.28-6.10 mu M) exhibited significant potency compared with clinically available anticancer drugs such as cisplatin (IC(5)0: 11.4-14.7 mu M) and etoposide (IC50: 1.2-21.2 mu M) on MDA-MB-231, MCF-7 and Jurkat cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.004

文献信息

• Simple approach to 1-O-protected (R)- and (S)-glycerols from l- and d-arabinose for glycerol nucleic acids (GNA) monomers research
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tetlet.2011.05.073

  日期：2011.7

  5-O-Protected (-Tr, -Sitert-BuPh2) d- and l-arabinofuranoses easily available in multigram quantities were converted to (S)- and (R)-1-O-protected glycerols, respectively, via oxidation (NaIO4) and reduction (NaBH4). Sources of chirality in the targets are the C4 atoms in the substrates. This stereospecific procedure permits a very simple access to both enantiomeric 1-O-protected glycerols for GNA

  5- O-保护的（-Tr，-Sitert-BuPh 2）d-和1-阿拉伯呋喃糖酶很容易以克数形式通过氧化作用分别转化为（S）和（R）-1- O保护的甘油。 NaIO 4）和还原（NaBH 4）。靶中的手性来源是底物中的C4原子。该立体特异性方法允许非常简单地获得两种对映体1- O-保护的甘油，以用于GNA单体工作。
• Synthesis of 6-<i>O</i>-octyl-β-<scp>D</scp>-galactopyranosyl-(1 → 5)-<scp>L</scp>-arabinose and comparative 1-deoxyglycitolation of <i>N</i>^α-Z-<scp>L</scp>-lysine with amphiphilic lipodisaccharides
  作者：Daniel Cabaret、Michel Wakselman

  DOI：10.1139/v90-347

  日期：1990.12.1

  A lipodisaccharide possessing a reactive aldopentose unit, 6-O-octyl-β-D-galactopyranosyl-(1 → 5)-L-arabinose 6, was obtained by glycoside synthesis. To avoid a possible intramolecular acyl transfer, benzoyl protecting groups and mild conditions of detritylation were used in the preparation of the furanosyl acceptor. The reductive alkylation of N^α-Z-L-lysine was then studied and compared to that of previously prepared liposaccharides. In this reaction, amphiphilic five-membered hemiacetals are generally more reactive than their six-membered analogues. The newly prepared disaccharide is the most reactive of the series and also the easiest to prepare. Therefore this reagent has been selected for a future study on the chemical modification of enzymes and the use in organic solvents of the biocatalysts obtained. Keywords: liposaccharides, reductive alkylation.

  一种具有反应性醛基五糖单元的脂质糖，6-O-辛基-β-D-半乳糖苷-(1→5)-L-阿拉伯糖6，通过糖苷合成获得。为了避免可能的分子内酰基转移，制备呋喃糖受体时使用苯甲酰保护基和温和的去三苯甲基化条件。然后研究了Nα- Z-L-赖氨酸的还原烷基化反应，并与以前制备的脂质糖进行了比较。在这个反应中，两性五元半乙醇通常比它们的六元类似物更具反应性。新制备的二糖是系列中最具反应性的，也是最容易制备的。因此，这种试剂已被选定用于将来对酶的化学修饰和有机溶剂中获得的生物催化剂的使用的研究。关键词：脂质糖，还原烷基化。
• CABARET, DANIEL;WAKSELMAN, MICHEL, CAN. J. CHEM., 68,(1990) N2, C. 2253-2257
  作者：CABARET, DANIEL、WAKSELMAN, MICHEL

  DOI：——

  日期：——