1-O-p-nitrobenzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose | 63087-91-2

• 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: 1-O-p-nitrobenzoyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose
• 英文别名: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 4-nitrobenzoate；<4-Nitro-benzoyl>-；2,3,4,6-tetra-O-benzyl-1-O-(4-nitrobenzoyl)-beta-D-glucopyranose；[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 4-nitrobenzoate
• CAS: 63087-91-2
• 化学式: C₄₁H₃₉NO₉
• 分子量: 689.762
• InChiKey: IJTANGJQVDVKFH-GCKSPRBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  51
• 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：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 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 1-O-p-nitrobenzoyl-2,3,4,6-tetra-O-benzyl-β-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

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。
• Unusual anomeric rearrangement of para-nitrobenzoylxanthate d-glycosides: a new direct stereoselective access to α-thioglycosides from pyranose sugars
  作者：Adjou Ané、Solen Josse、Sébastien Naud、Vivien Lacône、Sandrine Vidot、Anaïs Fournial、Anirban Kar、Muriel Pipelier、Didier Dubreuil

  DOI：10.1016/j.tet.2006.03.024

  日期：2006.5

  A mild and general procedure for the synthesis of alpha-thioglycosides from glycopyranoses is described. The method involves the treatment of pyranose reductive sugar with sodium hydride, carbon disulfide, and p-nitrobenzoyl chloride, as a key step, to yield p-nitrobenzoyl-alpha-D-thioglycopyranose intermediates with high stereoselectivity, in a one-pot-two-step process. The interest of the strategy highlights a direct stereoselective access to ether-protected 1-thiol-alpha-D-glycopyranose derivatives (Gal, Glc, and Man) from pyranoses in the absence of anomeric 'Lewis acid' promoters. (c) 2006 Elsevier Ltd. All rights reserved.
• Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors
  作者：Nathan D. Gould、C. Liana Allen、Brandon C. Nam、Alanna Schepartz、Scott J. Miller

  DOI：10.1016/j.carres.2013.09.011

  日期：2013.12

  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.