6-O-trityl-D-galactose | 54325-28-9

• 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: 6-O-trityl-D-galactose
• 英文别名: (3R,4S,5R,6R)-6-[(triphenylmethoxy)methyl]oxane-2,3,4,5-tetrol；(3R,4S,5R,6R)-6-(trityloxymethyl)oxane-2,3,4,5-tetrol
• CAS: 54325-28-9
• 化学式: C₂₅H₂₆O₆
• 分子量: 422.478
• InChiKey: WMNZCEKHTHLIRQ-CYSUJIKDSA-N

物化性质

• 沸点：
  595.6±50.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  6-O-trityl-D-galactose 在 sodium periodate 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 4-O-formyl-2,3-O-isopropylidene-5-O-triphenylmethyl-D-lyxose
  参考文献：
  名称：

  An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells

  摘要：

  A highly efficient synthesis of the biologically important fluorescent probe dansyl alpha-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding alpha-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl alpha-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.02.014
• 作为产物：
  描述：

  6-O-trityl-D-talose 在 水 、 二正丁基氧化锡 作用下， 生成 6-O-trityl-D-galactose
  参考文献：
  名称：

  Epimerization of Carbohydrates via Stannylene Acetals. A Practical Synthesis of D-Talose

  摘要：

  When treated with Bu2SnO in a suitable solvent, reducing sugars preferentially form 1,2-O-stannylene acetals and, on prolonged treatment with a slight excess of the reagent at reflux temperature, they undergo epimerization. This allows simple preparation of rare monosaccharides from readily available, unprotected starting materials. The process is equilibrium driven, and the equilibrium is shifted largely in favor of structures having an axial hydroxyl group at position 2.

  DOI：

  10.1080/07328309808002337

文献信息

• Substituent effects on the regioselectivity of enzymatic acylation of 6-O-alkylglycopyranosides using Pseudomonas cepacia lipase
  作者：David A. MacManus、Evgeny N. Vulfson

  DOI：10.1016/0008-6215(95)00292-8

  日期：1995.12

  Abstract The regioselectivity of acylation of a range of 6- O -protected glycosides using Pseudomonas cepacia lipase in vinyl acetate was investigated. In general, α-glycosides were acylated at the O-2 position and β-glycosides were acylated at the O-3 position. The effects of varying the size/hydrophobicity of the O-6 and anomeric substituents on the regioselectivity of the reaction are discussed

  摘要研究了假单胞菌洋葱脂肪酶在乙酸乙烯酯中酰化一系列6-O-保护的糖苷的区域选择性。通常，α-糖苷在O-2位被酰化，而β-糖苷在O-3位被酰化。根据底物在酶活性位点上的结合，讨论了改变O-6和端基异构体取代基的大小/疏水性对反应区域选择性的影响。
• An Efficient Method for the Synthesis of 2,6-Branched Galacto-Oligo­saccharides and Its Applications to the Synthesis of Three Tetrasaccharides and a Hexasaccharide Related to the Arabinogalactans (AGs)
  作者：Jun Ning、Yuetao Yi、Zhe Yao

  DOI：10.1055/s-2003-42109

  日期：——

  An efficient method for the synthesis of 2,6-branched galacto-oligosaccharides has been developed by using 6-O-Ac-2,3,4-tri-O-Bz-α-d-galactopyranosyl trichloroacetimidate, 2,6-di-O-Ac-3,4-di-O-Bz-α-d-galactopyranosyl trichloroacetimidate and 2-O-Ac-3,4,6-tri-O-Bz-α-d-galactopyranosyl trichloroacetimidate as synthons. Three tetrasaccharides and a hexasaccharides related to AGs from plants were readily prepared using this method.

  通过使用6-O-Ac-2,3,4-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺、2,6-二-O-Ac-3,4-二-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺和2-O-Ac-3,4,6-三-O-Bz-α-d-半乳糖吡喃糖苷三氯乙酰亚胺作为合成砌块，开发了一种高效合成2,6-支化半乳寡糖的方法。利用这种方法，可以方便地制备与植物来源的AGs相关的三种四糖和一种六糖。
• Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation
  作者：Wayne Pilgrim、Ciaran O'Reilly、Paul Murphy

  DOI：10.3390/molecules180911198

  日期：——

  Analogues of glycolipids from Spingomonadacaece with O- and S- and SO2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells.

  来自Spingomonadacaece的糖脂类类似物，具有O-、S-和SO2-连接，通过TiCl4催化的螯合诱导的异构化进行了制备。其中包括具有O-和S-糖苷键的中间体异构化的例子，以及β-硫葡萄糖醇酸（β-糖苷硫醇）的异构化。β-O-葡萄糖醛酸酯和β-O-半乳糖醛酸酯的前体采用苯甲酰化三氯乙酰胺高效制备。β-糖苷硫醇是β-S-衍生物的前体。含有三唑的天然糖脂类模仿物使用CuI催化的叠氮烷炔环加成反应在THF中制备。当前正在评估这些糖脂抗原对iNKT细胞的影响。
• 피리미딘, 피라졸 및 피라졸로피리미딘 융합된 카보하이브리드 헤테로고리 화합물 라이브러리 및 이의 제조방법
  申请人：Seoul National University R&DB Foundation 서울대학교산학협력단(120070509242) Corp. No ▼ 114371-0009224BRN ▼119-82-03684

  公开号：KR101595939B1

  公开（公告）日：2016-02-19

  본 발명은 카보하이브리드 기반의 분자 골격에 피리미딘, 피라졸 및 피라졸로피리미딘이 융합된 카보하이브리드 헤테로고리 화합물 라이브러리에 관한 것이다.

  本发明涉及基于卡波混合物分子骨架的嘧啶、吡唑和吡唑嘧啶融合的卡波混合物杂环化合物库。
• Regiospecific Anomerisation of Acylated Glycosyl Azides and Benzoylated Disaccharides by Using TiCl₄
  作者：Mark Farrell、Jian Zhou、Paul V. Murphy

  DOI：10.1002/chem.201302572

  日期：2013.10.25

  5 equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N‐acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan

  当路易斯酸（例如TiCl 4或SnCl 4）与吡喃糖环的氧原子和另一个位点配位时，会促进螯合诱导的异构化，从而导致内环裂解和异构化为更稳定的异构体。在这项研究中，证明了区域特异性定点异构化。的TiCl 4（2.5当量）用于诱导15种反应性低的糖基叠氮化物和二糖底物的异构化，并获得高产率（＞ 75％）和立体选择性（α/β＞ 9∶1）。实例包括吡喃葡萄糖醛酸，吡喃葡萄糖醛酸和甘露吡喃醛酸酯以及N-乙酰化吡喃葡萄糖醛酸和吡喃葡萄糖醛酸酯衍生物。包括在聚半乳糖醛酸中发现的具有α1→4键的二糖。已发现使用苯甲酰化的糖类在二糖异构化中非常重要，因为尝试使相关的乙酰基保护的2,3-碳酸酯保护的衍生物异构化的尝试并不成功。