3-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 17042-34-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 3-methylphenyl-tetra-O-acetyl-β-D-glucopyranoside；β-<3-Methyl-phenyl>-tetra-O-acetyl-D-glucopyranosid；m-tolyl-(tetra-O-acetyl-β-D-glucopyranoside)；m-Tolyl-(tetra-O-acetyl-β-D-glucopyranosid)；3-methylphenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3-methylphenoxy)oxan-2-yl]methyl acetate
• CAS: 17042-34-1
• 化学式: C₂₁H₂₆O₁₀
• 分子量: 438.431
• InChiKey: TVVBZWZUAIZRAV-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 氨 作用下， 生成 m-Kresyl-β-D-glucopyranosid
  参考文献：
  名称：

  Ramart-Lucas; Rabate, Bulletin de la Societe Chimique de France, 1935, vol. <5> 2, p. 1596,1605

  摘要：

  DOI：
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 生成 3-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  NOVIK, E. R.;SOKOLOV, V. M.;ZAXAROV, V. I.;STUDENTSOV, E. P.

  摘要：

  DOI：

文献信息

• Revisit of the phenol O-glycosylation with glycosyl imidates, BF3·OEt2 is a better catalyst than TMSOTf
  作者：Yali Li、Huaping Mo、Gaoyan Lian、Biao Yu

  DOI：10.1016/j.carres.2012.09.025

  日期：2012.12

  With BF(3)·OEt(2) as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent

  以BF（3）·OEt（2）为催化剂，苯酚与带有2-O-参与基团的糖基三氯乙酰基亚氨酸盐（或N-苯基三氟乙酰基亚氨酸盐）的糖基化反应通常会产生所需的1,2-反式-O-糖苷极佳的收率，而不会形成1,2-顺式端基异构体。然而，以TMSOTf为催化剂，相应的酚O-糖基化的结果高度依赖于酚的亲核性。苯酚的亲核性越少，生成的1，2-顺式-O-糖苷含量越高，副产物就越多。在所有这些酚O-糖基化反应中，发现1,2-原酸酯是低温（<-70°C）的主要产物，在较高温度下转化为最终产物。BF（3）·OEt（2）是促进1转化的有效催化剂 将2-原酸酯转化为相应的1，2-反式-O-糖苷。然而，在TMSOTf存在下，1,2-原酸酯可被转化为三氟甲磺酸二恶唑鎓和三氟甲磺酸糖基酯，这些中间体可能与糖基氧碳鎓相关物种处于平衡状态，最终形成α/β-O-的最终混合物。苷和副产物。
• Novik, E. R.; Sokolov, V. M.; Studentsov, E. P., Journal of general chemistry of the USSR, 1986, p. 159 - 165
  作者：Novik, E. R.、Sokolov, V. M.、Studentsov, E. P.、Zakharov, V. I.、Lavrent'ev, A. N.

  DOI：——

  日期：——
• ——
  作者：V. M. Sokolov、V. I. Zakharov、E. P. Studentsov

  DOI：10.1023/a:1019532924135

  日期：——

  C-13 NMR spectroscopy was used to study the stereoselectivity of glycosylation of phenols with the alpha and beta anomers of penta-O-acetyl-D-glucopyranose, penta-O-trifluoroacetyl-D-glucopyranose, and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-D-glucopyranose in the presence of boron trifluoride etherate at varied temperature, time, and catalyst amount. The boron trifluoride etherate-catalyzed reaction of penta-O-acetyl-beta-D-glucopyranose and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-beta-D-glucopyranose with phenols occurs with a high stereocontrol to give, depending on conditions, predominantly 1,2-cis- or 1,2-trans-aryl-glycosides. This reaction can be used for preparative synthesis of the alpha- and beta-anomeric forms of glycosides of a wide range of phenols.
• Kariyone et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 13
  作者：Kariyone et al.

  DOI：——

  日期：——
• Helferich; Philipp, Justus Liebigs Annalen der Chemie, 1934, vol. 514, p. 228,231
  作者：Helferich、Philipp

  DOI：——

  日期：——