2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl benzoate | 63053-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl benzoate
• 英文别名: 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose；[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] benzoate
• CAS: 63053-84-9
• 化学式: C₄₁H₄₀O₇
• 分子量: 644.764
• InChiKey: BNLYQEYFEOJREM-GCKSPRBUSA-N

物化性质

• 沸点：
  739.0±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl benzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以91%的产率得到苯甲酰基 beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Bols, Mikael; Hansen, Henrik Claus, Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 818 - 822

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl benzoate
  参考文献：
  名称：

  Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors

  摘要：

  Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Bronsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.09.011

文献信息

• Glycosyl<i>ortho</i>-Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group
  作者：Steffan K. Kristensen、Stéphane Salamone、Michelle R. Rasmussen、Mikkel H. S. Marqvorsen、Henrik H. Jensen

  DOI：10.1002/ejoc.201600747

  日期：2016.11

  p-cyano-o-methoxybenzoate donors. In glycosylation reactions with o-methoxybenzoate donors, the yields of disaccharide products were good to excellent for various glycosyl acceptors, including a carbohydrate-based secondary alcohol. Furthermore, β-selective mannosylation was achieved with a Crich-type donor at 0 °C to ambient temperature, without donor preactivation. The donor was also used for the first

  我们将 β-邻甲氧基苯甲酸酯描述为一种用于催化化学糖基化的储存稳定且实用的 C-1 核离心剂，其中苯甲酸副产物可以很容易地去除、重新分离，并可能在糖基化反应后回收。这种新型糖基供体可以通过一系列促进剂有效活化，包括 Bi(OTf)3、Fe(OTf)3、TMSOTf（TMS = 三甲基甲硅烷基）和三氟甲磺酸，催化剂用量低（<10 mol-%）负荷。供体显示出比类似的苯甲酸盐、对甲氧基苯甲酸盐和对氰基-邻甲氧基苯甲酸盐供体更高的反应性。在与邻甲氧基苯甲酸酯供体的糖基化反应中，对于各种糖基受体（包括基于碳水化合物的仲醇），二糖产物的产率从好到极好。此外，β-选择性甘露糖基化是用 Crich 型供体在 0°C 至环境温度下实现的，无需供体预活化。供体也用于一锅两步糖基化的第一步，得到三糖；第二个偶联涉及用 NIS/TMSOTf（NIS = N-碘代琥珀酰亚胺）激活硫糖苷。我们相信这为当前协议提供了一个很好的替代方案。
• Syntheses of 1-O-acylaldose derivatives via the corresponding O-glycosylpseudoureas
  作者：Hideo Tsutsumi、Yoshiharu Ishido

  DOI：10.1016/0008-6215(82)85008-8

  日期：1982.12

  Abstract A series of 1- O -acylaldose derivatives was prepared in good yield through the reaction of 1,3-dialkyl- O -glycosylpseudoureas with carboxylic acids.

  摘要通过1，3-二烷基-O-糖基假单胞菌与羧酸的反应，高收率地制备了一系列1-O-酰基醛糖衍生物。
• An efficient synthesis of glycosyl esters exploiting the mitsunobu reaction.
  作者：Amos B. Smith、Karl J. Hale、Ralph A. Rivero

  DOI：10.1016/s0040-4039(00)85334-4

  日期：1986.1

  The anomeric hydroxyl group of various pyranose hemiacetals can be esterified with inversion of configuration, conveniently, mildly and on large-scale using triphenylphosphine (TPP), with either diisopropylazodicarboxylate (DIAD) or diethylazodicarboxylate (DEAD) and a carboxylic acid in THF at either −50° C or at room temperature.

  各种吡喃糖半缩醛的异头羟基可以使用三苯基膦（TPP），偶氮二甲酸二异丙酯（DIAD）或偶氮二甲酸二乙酯（DEAD）和羧酸在THF中的构型反转，方便，温和且大规模地酯化- 50°C或在室温下。
• STEREOSELECTIVE SYNTHESIS OF 1-<i>O</i>-ACYL-D-GLUCOPYRANOSE FROM 1-HYDROXY SUGAR AND ACYL FLUORIDES BY THE PROMOTION OF CESIUM FLUORIDE
  作者：Shin-ichiro Shoda、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.861

  日期：1982.6.5

  In the presence of cesium fluoride, the reaction of 2,3,4,6-tetra-O-benzyl-d-glucopyranose with acyl fluorides affords the corresponding glucosyl esters in good yields under essentially neutral condition. The α⁄β ratio of produced glucosyl esters is greatly affected by reaction conditions and predominant formations of each anomer is achieved by procedures described herein.

  在氟化铯存在下，2,3,4,6-四-O-苄基-d-吡喃葡萄糖与酰氟反应在基本中性条件下以良好的产率提供相应的葡萄糖酯。所产生的葡萄糖酯的α/β比率很大程度上受反应条件影响，并且每种端基异构体的主要形成是通过本文描述的程序实现的。
• Metal-Free Synthesis of Acyl Glycosides and Application to Oligosaccharide Synthesis
  作者：Koji Morimoto、Kana Yanase、Tetsuya Kajimoto、Yasuyuki Kita

  DOI：10.1021/acs.orglett.2c03661

  日期：2022.12.16

  Oligosaccharides are involved in numerous biological processes. Achieving optimal anomeric selectivity and regioselectivity remains challenging. Herein, we present a method for the oxidative glycosylation of thioglycosides with hypervalent iodine reagents derived from carboxylic acid to form C–O bonds. The reaction of thioglycosides with various hypervalent iodine carboxylates afforded acyl O-glycosyl

  寡糖参与许多生物过程。实现最佳端基异构选择性和区域选择性仍然具有挑战性。在此，我们提出了一种硫苷氧化糖基化与衍生自羧酸的高价碘试剂形成 C-O 键的方法。硫代糖苷与各种高价碘羧酸盐反应得到酰基O-糖基化合物。这些酰基O-糖基化合物可与硫糖苷受体反应生成二糖；重复该方法可合成三糖和四糖。