1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose | 63028-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
• 英文别名: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl benzoate；[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] benzoate
• CAS: 63028-91-1
• 化学式: C₄₁H₄₀O₇
• 分子量: 644.764
• InChiKey: BNLYQEYFEOJREM-ZWWYPIQLSA-N

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：

  1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 在 palladium on activated charcoal 甲酸 作用下， 以 甲醇 为溶剂， 生成 1-O-benzoyl-α-D-glucopyranose
  参考文献：
  名称：

  Removal of O-benzyl protecting-groups of carbohydrate derivatives by catalytic, transfer hydrogenation

  摘要：

  DOI：

  10.1016/s0008-6215(00)85381-1
• 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 氘代氯仿 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
  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
• 作为试剂：
  描述：

  4-碘苯甲醚 在 乙二醇二甲醚溴化镍 、 (C₅H₅)2Zr(OC₄H₈)N(Si(CH₃)3)CH(C₆H₅) 、 1-O-benzoyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 、 (4R,4’R)-4,4’-二异丙基-4,4’,5,5’-四氢-2,2’-双噁唑 作用下， 以 四氢呋喃 为溶剂， 以24 %的产率得到4,4-二甲氧基联苯
  参考文献：
  名称：

  锆氮丙啶介导的镍催化非对映选择性 C(sp2)-糖基化

  摘要：

  在有机合成领域，C-糖苷键的催化和立体选择性形成是连接碳水化合物和糖苷配基的关键过程。然而，糖支架的固有手性通常对手性配体施加的立体诱导具有重大影响。在这项研究中，我们建立了一种前所未有的锆氮丙啶介导的不对称镍催化作用，使得稳定的糖基磷酸酯与一系列（杂）芳香族和糖醛碘化物作为可行的亲电试剂进行非对映选择性偶联。我们开发的方法展示了广泛的范围和对各种官能团的高耐受性。更重要的是，通过在这种还原镍催化中简单地利用流行的手性二恶唑啉（biOx）配体，可以实现对形成C（sp 2 ）-糖苷的两种异头构型的精确立体控制。关于操作机制，实验和计算研究都支持氧化还原金属转移过程的发生，导致瞬态双金属 Ni-Zr 物质的形成，在催化过程中充当有效且高效的单电子还原剂。

  DOI：

  10.1021/jacs.4c04587

文献信息

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

  DOI：——

  日期：——