1-adamantyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-adamantyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
• 英文别名: 1-adamantanol 2,3,4,6-tetra-O-benzyl-D-glucopyranoside；(3R,4S,5R,6R)-2-(1-adamantyloxy)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₄₄H₅₀O₆
• 分子量: 674.877
• InChiKey: ARSXFHWAVPYIDC-RLXDAORQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-adamantyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors

  摘要：

  Glycosyl (N-phenyl)trifluoroacetimidates, readily prepared from 1-hydroxyl sugars by treatment with (N-phenyl)trifluoroacetimidoyl chloride in the presence of K2CO3, were demonstrated to be effective glycosyl donors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00157-5

文献信息

• Lanthanoid(III) triflates as new glycosylation catalysts. Selective and efficient activation of 1-O-methoxyacetyl sugars
  作者：Junji Inanaga、Yasuo Yokoyama、Takeshi Hanamoto

  DOI：10.1016/s0040-4039(00)73563-5

  日期：1993.4

  The reactions of 1-O-methoxyacetyl sugars with alcohols or thiols were effectively promoted by a catalytic amount of lanthanoid(III) triflates such as Tb(OTf)3, Ho(OTf)3, Tm(OTf)3, and Yb(OTJ)3 to give the corresponding glycosides in good to excellent yields.

  催化量的镧系元素（III）三氟甲磺酸酯如Tb（OTf）3，Ho（OTf）3，Tm（OTf）3和Yb（OTJ ）有效地促进了1- O-甲氧基乙酰基糖与醇或硫醇的反应）3以良好至极好的产率得到相应的糖苷。
• A Streamlined Regenerative Glycosylation Reaction: Direct, Acid‐Free Activation of Thioglycosides
  作者：Samira Escopy、Yashapal Singh、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1002/chem.202003479

  日期：2021.1.4

  (HOFox) is able to mediate glycosylations via intermediacy of OFox imidates. Thioglycoside precursors were first converted into the corresponding glycosyl bromides that were then converted into the OFox imidates in the presence of Ag2O followed by the activation with catalytic Lewis acid in a regenerative fashion. Reported herein is a direct conversion of thioglycosides via the regenerative approach

  我们的小组之前曾报道过，3,3-二氟吲哚（HOFox）能够通过 OFox 亚胺酸酯的中介来介导糖基化。硫糖苷前体首先转化为相应的糖基溴化物，然后在 Ag 2 O存在下转化为 OFox 亚胺酸酯，然后以再生方式用催化路易斯酸活化。本文报道了通过再生方法直接转化硫糖苷，该方法绕过了溴化物的中介并消除了对基于重金属的促进剂的需要。在中性反应条件下仅使用 1 当量即可实现硫糖苷的直接再生活化。不含酸性添加剂的 NIS 和催化 HOFox。
• Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group
  作者：Hiroshi Imagawa、Atsushi Kinoshita、Takashi Fukuyama、Hirofumi Yamamoto、Mugio Nishizawa

  DOI：10.1016/j.tetlet.2006.04.114

  日期：2006.7

  A novel Hg(OTf)(2)-catalyzed glycosylation procedure has developed using alkynoic acid residues as the leaving group under mild reaction conditions and efficient catalytic turnover. The process is particularly useful for the glycosylation of hindered alcohols. (c) 2006 Elsevier Ltd. All rights reserved.
• Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors
  作者：Biao Yu、Houchao Tao

  DOI：10.1016/s0040-4039(01)00157-5

  日期：2001.3

  Glycosyl (N-phenyl)trifluoroacetimidates, readily prepared from 1-hydroxyl sugars by treatment with (N-phenyl)trifluoroacetimidoyl chloride in the presence of K2CO3, were demonstrated to be effective glycosyl donors. (C) 2001 Elsevier Science Ltd. All rights reserved.