2-pyridyl β-D-galactopyranoside | 347391-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-pyridyl β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-pyridin-2-yloxyoxane-3,4,5-triol
• CAS: 347391-61-1
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: FPCRLSXURVXMHL-WIAVHCEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-pyridyl β-D-galactopyranoside 在 咪唑 、 4-二甲氨基吡啶 、 pyridinium triflate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.25h， 生成 Benzoic acid (3aS,4R,6S,7R,7aS)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethoxy-2-methyl-6-(pyridin-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  参考文献：
  名称：

  Practical syntheses of B disaccharide and linear B type 2 trisaccharide—non-primate epitope markers recognized by human anti-α-Gal antibodies causing hyperacute rejection of xenotransplants

  摘要：

  Synthetic protocols are presented for the elaboration of Gal alpha1 --> 3GalOR and Gal alpha1 --> 3Gal beta1 --> 4GlcNAcOR di- and trisaccharides that use a common Gal donor/acceptor unit, and are potentially adaptable to scale-up. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00196-x
• 作为产物：
  描述：

  2-羟基吡啶银盐 在 甲醇 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 2-pyridyl β-D-galactopyranoside
  参考文献：
  名称：

  2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol

  摘要：

  2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent glycosylation reactions smoothly to produce the coupled products in high yields. Furthermore, the 2-pyridyl glycosides were applied to the efficient oligosaccharide assembly by the preactivation-based one-pot oligosaccharide synthesis protocol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.066

文献信息

• Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes
  作者：Lars Kröger、Joachim Thiem

  DOI：10.1016/j.carres.2006.10.014

  日期：2007.2

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.