4-O-Acetyl-3,6-di-O-benzyl-D-glucal | 165524-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-Acetyl-3,6-di-O-benzyl-D-glucal
• 英文别名: [(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-yl] acetate
• CAS: 165524-87-8
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: GMASVJJCGAIRIV-VSKRKVRLSA-N

物化性质

• 沸点：
  484.7±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-O-Acetyl-3,6-di-O-benzyl-D-glucal 在 2,3,5-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 bisdicollidine iodonium perchloride 、 氨 、 水 、 sodium 、 碳酸氢铵 、 1-羟基苯并三唑 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide

  摘要：

  DOI：

  10.1002/1521-3773(20001016)39:20<3652::aid-anie3652>3.0.co;2-b
• 作为产物：
  描述：

  乙酸酐 、 3,6-Di-O-苯甲基-D-葡萄醛 在 吡啶 作用下， 反应 10.0h， 以100%的产率得到4-O-Acetyl-3,6-di-O-benzyl-D-glucal
  参考文献：
  名称：

  Preparation of Building Blocks for Carba‐Oligosaccharides: Some Protected 5a′‐Carba‐D‐hexopyranosyl‐1,5‐anhydro‐2‐deoxy‐D‐arabino‐hex‐1‐enitols, and 5a,5a′‐Dicarba Congeners Thereof

  摘要：

  Four configurational types of two protected O -linked (5a-carba-D-hexopyranosyl)-D-glucal and carba-D-glucal derivatives were prepared in order to provide versatile synthetic intermediates readily convertible into carba-oligosaccharides of biological interest. These compounds may also find application as donors for elongation of carba-oligosaccharide chains having O -linked carbahexopyranose residues at nonreducing ends.

  DOI：

  10.1080/07328300600572907

文献信息

• Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides
  作者：Benjamin D. Sherry、Rebecca N. Loy、F. Dean Toste

  DOI：10.1021/ja031895t

  日期：2004.4.1

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.
• A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant
  作者：Zhi-Guang Wang、J. David Warren、Vadim Y. Dudkin、Xufang Zhang、Ulrich Iserloh、Michael Visser、Matthias Eckhardt、Peter H. Seeberger、Samuel J. Danishefsky

  DOI：10.1016/j.tet.2006.02.080

  日期：2006.5

  The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15 -> 18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34 -> 36). Another key strategic element involved the epimerization of an interior core glucoside to reach the P-mannoside (see 37 -> 38) required in the ring C sugar of the high mannose core. (c) 2006 Elsevier Ltd. All rights reserved.
• Adducts of uridine and glycals as potential substrates for glycosyltransferases
  作者：Ilona Wandzik、Tadeusz Bieg

  DOI：10.1016/j.bioorg.2007.07.001

  日期：2007.10

  We report on the synthesis of 2-deoxyglycosyl derivatives of uridine as potential donor substrates for glycosyltransferases. The totally stereoselective synthesis is accomplished by two sequential addition reactions of uridine derivatives to glycals promoted by triphenylphosphine-hydrogen bromide. (c) 2007 Elsevier Inc. All rights reserved.
• Fischer, Susanne; Hamann, Carl Heinz, Journal of Carbohydrate Chemistry, 1995, vol. 14, # 3, p. 327 - 340
  作者：Fischer, Susanne、Hamann, Carl Heinz

  DOI：——

  日期：——
• A Highly Convergent Total Synthetic Route to Glycopeptides Carrying a High-Mannose Core Pentasaccharide DomainN-linked to a Natural Peptide Motif
  作者：Samuel J. Danishefsky、Shuanghua Hu、Pier F. Cirillo、Matthias Eckhardt、Peter H. Seeberger

  DOI：10.1002/chem.19970031011

  日期：1997.10

  AbstractN‐Linked glycopeptides were synthesized by condensation of a highmannose anomeric amine bearing a pentasaccharide with aspartic‐acid‐containing tri‐ and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the „core”︁ region of all asparagine‐linked glycoproteins, was assembled by means of glycal‐derived thioethyl donors and glycal acceptors. The central mannose residue was established by inversion of the C2 hydroxyl of a glucosyl precursor in the pentasaccharide. The protecting‐group scheme employed allows the extension of the pentasaccharide through the terminal mannose units. While a fully convergent coupling of the high‐mannose carbohydrate to the peptide domain has thus been accomplished for the first time with a fully synthetic sugar, the stereochemical integrity of the anomeric center of the carbohydrate domain was not maintained and a mixture of glycopeptides was obtained.