methyl 3-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)propyl ketone | 102219-30-7

• 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: methyl 3-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)propyl ketone
• 英文别名: [(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-(3-oxobutyl)oxan-2-yl]methyl acetate
• CAS: 102219-30-7
• 化学式: C₁₈H₂₆O₁₀
• 分子量: 402.398
• InChiKey: DAYIHQUXPHZSJD-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  丁烯酮 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 Ru(bpy)₃(BF₄)₂ 、 二氢吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到methyl 3-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)propyl ketone
  参考文献：
  名称：

  可见光介导的分子间糖基卤化物与烯烃的加成反应

  摘要：

  捕获光子：可见光，胺还原剂和[Ru（bpy）3 ] 2+光催化剂可用于介导将糖基卤化物添加到烯烃中以合成重要的C-糖苷（请参见方案）。这种方法显示出光催化有效地驱动有用和困难的化学转化的潜力越来越大。

  DOI：

  10.1002/anie.201004311

文献信息

• Synthesis of -glycosyl compounds by the addition of glycosyl radicals to olefins
  作者：Younosuke Araki、Tadatoshi Endo、Masaki Tanji、Jun'ichi Nagasawa、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(01)81072-8

  日期：1987.1

  The Bu3SnH - AIBN induced radical additions of 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl derivatives, bearing α-Br (1), α-I (5) β-OCSSMe (7), and β-SePh (8) groups on the anomeric carbon, with olefins such as dimethyl maleate, methyl vinyl ketone, dimethyl acetylenedicarboxylate, butyl vinyl ether, and -ethylmaleimide were examined for a synthesis of -glycosyl compounds.

  Bu 3 SnH-AIBN诱导的带有α-Br（1），α-I（5）β-OCSSMe（7）的2,3,4,6-四-O-乙酰基-D-吡喃葡萄糖基衍生物的自由基加成，检查了异头碳上的β-SePh（8）基团和烯烃，例如马来酸二甲酯，甲基乙烯基酮，乙炔二羧酸二甲酯，丁基乙烯基醚和-乙基马来酰亚胺，以合成-糖基化合物。
• Conjugate additions of alkylchromium reagents mediated by chromium(III) chloride/manganese
  作者：Jacques Augé、Richard Gil、Sophie Kalsey

  DOI：10.1016/s0040-4039(98)80021-x

  日期：1999.1

  Benzyl and glycosylchromium reagents generated from the corresponding halides and the couple Cr(III)/Mn were added to activated alkenes to afford Michael adducts. The influence of a ligand around the chronium atom as well as the use of a catalytic amount of chromium chloride were investigated.

  由相应的卤化物和成对的Cr（III）/ Mn生成的苄基和糖基铬试剂被添加到活化的烯烃中，得到迈克尔加合物。研究了配体对around原子的影响以及催化量氯化铬的使用。
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• Titanium(III)-Promoted Stereoselective Synthesis of Simple <i>C</i>-Glycosides
  作者：Roxanne P. Spencer、Jeffrey Schwartz

  DOI：10.1021/jo9702352

  日期：1997.6.1