Methyl 2,6-di-O-acetyl-β-D-galactopyranoside | 51842-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,6-di-O-acetyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 51842-26-3
• 化学式: C₁₁H₁₈O₈
• 分子量: 278.259
• InChiKey: JMLKJIAWZMOPNB-ZKKRXERASA-N

物化性质

• 沸点：
  388.5±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,6-di-O-acetyl-β-D-galactopyranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 19.67h， 生成 [(2S,3R,4S,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-methoxyoxan-4-yl]oxyoxan-3-yl] benzoate
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z
• 作为产物：
  描述：

  methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 在 吡啶 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.08h， 生成 Methyl 2,6-di-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.

  DOI：

  10.1016/0008-6215(93)80006-z

文献信息

• Enzyme-Catalyzed Regioselective Acetylation of Functionalized Glycosides
  作者：Thomas Holmstrøm、Christian Marcus Pedersen

  DOI：10.1002/ejoc.202000696

  日期：2020.8.9

  A wide range of functionalized mono‐saccharides has been regioselectively 3,6‐acetylated using a commercially available enzyme. The enzyme tolerates different anomeric groups and stereochemistry of the sugar, making the method highly attractive for building block synthesis. The reaction works under neat conditions and also with green solvents and hence halogenated solvents, heavy metal reagents, and

  使用市售酶已对多种功能化的单糖进行了区域选择性3,6-乙酰化。该酶耐受糖的不同端基异构体和立体化学，使该方法对构建基块合成具有高度吸引力。该反应在纯净的条件下进行，并且还可以使用绿色溶剂，因此可以避免使用卤代溶剂，重金属试剂，并且可以避免多次反应。
• Synthesis of GD3-lactam: a potential ligand for the development of an anti-melanoma vaccine
  作者：Nafizal Hossain、Amparo Zapata、Mikael Wilstermann、Ulf J. Nilsson、Göran Magnusson

  DOI：10.1016/s0008-6215(02)00036-8

  日期：2002.4

  The novel sialyl donor methyl (ethyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-2-thio-3-thiophenyl-D-erthro-beta-L-gluco-non-2-ulopyranosid)onate was used for glycosylation of a lactosyl acceptor to give the GM3-trisaccharide derivative in 83% yield. Introduction of an azido group at C-9" of the GM3-trisaccharide derivative, transformation into a glycosyl acceptor, and sialylation with the above mentioned novel sialyl donor gave a GD3-trisaccharide in 50% yield. Reduction of the azido group gave the corresponding amine, which underwent spontaneous lactamization to the GD3-[1'''-9"]-lactam in an overall yield of 86%. Removal of protecting groups of over five steps, followed by per-O-acetylation gave an acetylated GD3-[1'''-9"]-lactam TMSEt glycoside in 27% overall yield. The acetylated GD3-[1'''-9"]-lactam TMSEt glycoside is suitable for glycosylation of linker-arms and the resulting linker-glycosides are planned to be coupled to carrier proteins. thus providing immunogens for trial vaccinations against malignant melanoma. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Investigation of the Stability of Thiosialosides toward Hydrolysis by Sialidases Using NMR Spectroscopy
  作者：Jennifer C. Wilson、Milton J. Kiefel、Donald I. Angus、Mark von Itzstein

  DOI：10.1021/ol990652w

  日期：1999.8.1

  H-1 NMR spectroscopy has been used to investigate whether the alpha(2-->6)-linked thiosialoside 3 and the alpha(2-->3)-linked thiosialoside 9 are hydrolyzed in the presence of Vibrio cholerae sialidase, Similarly, the hydrolysis of the O-ketosides Neu5Ac-2-O-alpha-(2-->3)-Gal beta Me (4) and the alpha-(2-->6)-sialyllactoside 7, representing natural alpha(2-->3)- and alpha(2-->6)-linked sialosides, respectively, was investigated. The results of the H-1 NMR experiments clearly demonstrate that the thiosialosides are not hydrolyzed by Vibrio cholerae sialidase, As expected, the O-sialosides are hydrolyzed to give N-acetyl-alpha-D-neuraminic acid as the first product of substrate cleavage.
• Calvo-Asin, Jose A.; Calvo-Flores, Francisco G.; Exposito-Lopez, Juan M., Journal of the Chemical Society. Perkin transactions I, 1997, # 8, p. 1079 - 1081
  作者：Calvo-Asin, Jose A.、Calvo-Flores, Francisco G.、Exposito-Lopez, Juan M.、Hernandez-Mateo, Fernando、Garcia-Lopez, Juan J.、Isac-Garcia, Joaquin、Santoyo-Gonzalez, Francisco、Vargas-Berenguel, Antonio

  DOI：——

  日期：——
• BETANELI, V. I.;KRYAZHEVSKIX, I. A.;OTT, A. YA.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 15,(1989) N, S. 217-230
  作者：BETANELI, V. I.、KRYAZHEVSKIX, I. A.、OTT, A. YA.、KOCHETKOV, N. K.

  DOI：——

  日期：——