methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 145251-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: Gal2Ac3Ac4Ac6Ac(b1-3)b-Glc1Me2Ac4Ac6Ac；[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-6-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 145251-16-7
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: UHSQXNOZAXQAJT-FDXOKOSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99.8%的产率得到Methyl 3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Sadozai, Khalid Khan; Anand, Jasbir Kaur; Hakomori, Sen-itiroh, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 7, p. 1037 - 1050

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-β-D-glucopyranoside 4,6-diacetate 在 palladium on activated charcoal 吡啶 、 4 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 26.0h， 生成 methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Sadozai, Khalid Khan; Anand, Jasbir Kaur; Hakomori, Sen-itiroh, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 7, p. 1037 - 1050

  摘要：

  DOI：

文献信息

• Fast and efficient synthesis of a novel homologous series of l-fucosylated trisaccharides using the Helix pomatia α-(1→2)-l-galactosyltransferase
  作者：Angela Michelle Scheppokat、Hagen Bretting、Joachim Thiem

  DOI：10.1016/s0008-6215(03)00344-6

  日期：2003.9

  The alpha-(1-->2)-L-galactosyltransferase from the albumen gland of the vineyard snail Helix pomatia exhibits high alpha-(1-->2)-L-fucosyltransferase activity and can be used to transfer L-fucose from GDP-L-fucose to terminal, non-reducing D-galactose residues of an oligosaccharide, thus providing facile access to a range of H-antigen-containing oligosaccharides. The enzymatic glycosylation was applied

  来自葡萄园蜗牛螺旋藻的蛋白腺的α-（1-> 2）-L-半乳糖基转移酶表现出高的α-（1-> 2）-L-岩藻糖基转移酶活性，可用于从中转移L-岩藻糖GDP-L-岩藻糖可连接至寡糖的末端非还原D-半乳糖残基，因此可轻松接入各种含H抗原的寡糖。酶促糖基化在这里以毫克级施加到一系列二糖受体底物上。显然，末端和亚末端受体糖单元之间糖苷间键合的位置几乎没有影响。由此产生的三糖的同源系列通过其过乙酸盐的NMR分析得到充分表征。
• Determination of the Conformational Flexibility of Methyl α-Cellobioside in Solution by NMR Spectroscopy and Molecular Simulations
  作者：E. Andreas Larsson、Mikael Staaf、Peter Söderman、Christer Höög、Göran Widmalm

  DOI：10.1021/jp049714c

  日期：2004.5.1

  The conformational flexibility of methyl alpha-cellobioside in water and dimethyl sulfoxide solutions was investigated by 1D H-1, H-1 T-ROESY experiments. In combination with molecular dynamics simulations, effective proton-proton distances could be derived using experimentally determined cross-relaxation rates. An anti-Psi-conformational state was present in both solvents confirming a previous flexibility hypothesis at this torsion angle. In water solution, an anti -Phi-conformational state was also detected and quantified. These results show that already at the disaccharide level a large flexibility is present at the glycosidic linkage. In addition to the syn-conformation which is present to similar to93% for the title compound in water solution, the minor anti-Phi- and anti-Psi-conformational states are populated to similar to2% and similar to5%, respectively.
• Reactivity of sugar trityl ethers in trityl?cyanoalkylidene condensation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00699016

  日期：1993.11

  The reactivity of a series of primary and secondary sugar trityl ethers in trityl-cyanoalkylidene condensation has been determined. It was found that the stereoselectivity of glycosylation by this method does not directly depend on the reactivity of the trityl ethers. Based on the results obtained, a stepwise mechanism rather than a concerted mechanism has been chosen as the most probable.
• Linear dependence of the glycosylation stereoselectivity ofO-trityl ethers by carbohydrate 1,2-O-cyanoalkylidene derivatives on anion concentrations. Effect of substituents in the glycosyl acceptor and a new mechanism of 1,2-cis-glycosides formation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00707066

  日期：1995.6

  The dependence of the stereochemical outcome of trityl-cyanoalkylidene condensation (alpha/beta-ratio of disaccharides) on the concentration of a catalyst (TrClO(4)) was studied. The dependence was shown to be linear over a wide range of concentrations of the catalyst. The mechanism of the reaction and the effect of the nature of protective groups in the glycosyl acceptor on the stereochemistry of glycosylation are discussed. A new mechanism of 1,2-cis-glycosides formation is proposed.