2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 100336-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-pyridin-2-yloxyoxan-2-yl]methyl acetate
• CAS: 100336-51-4
• 化学式: C₁₉H₂₃NO₁₀
• 分子量: 425.392
• InChiKey: RTISUDKFHVAOHW-WRNCNIFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.25h， 生成 (3aS,4R,6S,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-dimethylamino-2-methyl-6-(pyridin-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol
  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：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 、 2-羟基吡啶 在 C₁₆H₂₈AgN₄⁽¹⁺⁾ 、 苄基三乙基氯化铵 作用下， 反应 3.33h， 以51%的产率得到2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids

  摘要：

  We herein report O-glycosidation reactions promoted via silver N-heterocyclic carbene complexes formed in situ in ionic liquids. Seven different room temperature ionic liquids were screened for the glycosidation reaction of 4-nitrophenol with tetra-O-acetyl-alpha-D-galactopyranosyl bromide. Good to excellent yields were obtained using Ag-NHC complexes derived from imidazolium halide salts to promote the glycosidation reaction, whereas yields considered moderate to low were obtained without use of the silver carbene complex. Anion metathesis of the ionic liquids with inexpensive alkylammonium halides also resulted in silver N-heterocyclic carbene formation and subsequent O-glycosidation in the presence of silver carbonate. Effective utility of this methodology has been demonstrated with biologically relevant acceptors (including flavones and steroids) where O-beta-glycoside products were obtained selectively in moderate to good yields. We have also demonstrated that the Ag-NHC complex is a superior promoter to traditionally used silver carbonate for the glycosidation of polyphenolic acceptors. The ionic liquids used in the study could be recycled three times without apparent loss in activity. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2011.03.007

文献信息

• An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.carres.2009.03.010

  日期：2009.5

  Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.
• 2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol
  作者：De-Cai Xiong、An-Qi Yang、Yang Yu、Xin-Shan Ye

  DOI：10.1016/j.tetlet.2014.11.066

  日期：2015.1

  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.
• 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.