p-chlorophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 32742-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-chlorophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-chlorophenoxy)oxan-2-yl]methyl acetate
• CAS: 32742-23-7
• 化学式: C₂₀H₂₃ClO₁₀
• 分子量: 458.85
• InChiKey: SALMOSOXXNZOJP-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  对氯苯酚 、 α-D(+)-五乙酰葡萄糖 在 zinc(II) chloride 作用下， 生成 p-chlorophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  A Suggestion on the Application of Hudson's Isorotation Rules¹

  摘要：

  DOI：

  10.1021/ja01140a026

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。
• GLYCOSYLTRANSFERASE REVERSIBILITY FOR SUGAR NUCLEOTIDE SYNTHESIS AND MICROSCALE SCANNING
  申请人：Thorson Jon S.

  公开号：US20130004979A1

  公开（公告）日：2013-01-03

  The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

  本发明一般涉及利用糖基转移酶可逆性合成核苷酸二磷酸（NDP）糖的材料和方法。本发明提供了改良反应可逆性并扩展糖供体特异性的工程糖基转移酶酶，与相应的非突变糖基转移酶酶相比，具有更好的反应可逆性和扩展的糖供体特异性。这些试剂提供了有利的NDP糖路线，用于随后在各种生物医学应用中使用，包括酶促和化学酶促糖随机化。
• Yamaguchi, Masahiko; Horiguchi, Akira; Fukuda, Akira, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1079 - 1082
  作者：Yamaguchi, Masahiko、Horiguchi, Akira、Fukuda, Akira、Minami, Toru

  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.
• Sinha, Bharati; Pansare, V. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 825 - 826
  作者：Sinha, Bharati、Pansare, V. S.

  DOI：——

  日期：——