3-Deoxy-1,2-O-isopropylidene-5,6-O-(2-phenylsulfonyl)ethylidene-α-D-glucofuranose | 280557-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Deoxy-1,2-O-isopropylidene-5,6-O-(2-phenylsulfonyl)ethylidene-α-D-glucofuranose
• 英文别名: (3aR,5S,6aR)-5-[(4R)-2-(benzenesulfonylmethyl)-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 280557-42-8
• 化学式: C₁₇H₂₂O₇S
• 分子量: 370.423
• InChiKey: LAZVZOLXZRVZQT-QCFNQLOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Deoxy-1,2-O-isopropylidene-5,6-O-(2-phenylsulfonyl)ethylidene-α-D-glucofuranose 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以82%的产率得到3-deoxy-1,2-O-isopropylidene-6-O-[(E)-2'-(phenylsulfonyl)vinyl]-α-D-glucofuranose
  参考文献：
  名称：

  Carbohydrate-derived PSE acetals: controlled base-induced ring cleavage

  摘要：

  Retro-Michael type reactions applied to PSE acetals protecting monosaccharides led either to complete removal or to ring-cleavage. In protic medium, application of standard basic conditions resulted in acetal deprotection, while the use of butyl lithium in aprotic medium allowed controlled ring-cleavage. A regio-and stereoselective C- over O-alkylation was observed during the process. Furthermore, depending on the substrates and the reaction conditions involved, new carbohydrate-derived beta-alkoxyvinyl sulfones were obtained with varying regioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.009
• 作为产物：
  描述：

  1,2-bis(phenylsulfonyl)ethylene 、 3-deoxy-1,2-O-isopropylidene-D-glucose 在 potassium tert-butylate 、 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 以94%的产率得到3-Deoxy-1,2-O-isopropylidene-5,6-O-(2-phenylsulfonyl)ethylidene-α-D-glucofuranose
  参考文献：
  名称：

  Phenylsulfonylethylidene (PSE) Acetals: A Novel Protective Group in Carbohydrate Chemistry

  摘要：

  一系列糖衍生的苯基磺酰乙烯亚胺醛醚在碱性条件下容易从相应的二醇和1,2-双（苯基磺酰）乙烯获得。对此类醚的去保护方法也进行了研究。

  DOI：

  10.1055/s-2001-10817

文献信息

• Phenylsulfonylethylidene (PSE) acetals as atypical carbohydrate-protective groups
  作者：Florence Chéry、Patrick Rollin、Ottorino De Lucchi、Sergio Cossu

  DOI：10.1016/s0040-4039(00)00199-4

  日期：2000.4

  We introduce a new class of arylsulfonylated cyclic acetals derived from carbohydrate structures which are synthesized with high yields under basic conditions. Deprotection methods for such acetals are also investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Phenylsulfonylethylidene (PSE) Acetals: A Novel Protective Group in Carbohydrate Chemistry
  作者：Florence Chéry、Patrick Rollin、Ottorino De Lucchi、Sergio Cossu

  DOI：10.1055/s-2001-10817

  日期：——

  A range of sugar-derived phenylsulfonylethylidene acetals were easily obtained from the corresponding diols and 1,2-bis(phenylsulfonyl)ethylene under basic conditions. Deprotection methods for such acetals have also been investigated.

  一系列糖衍生的苯基磺酰乙烯亚胺醛醚在碱性条件下容易从相应的二醇和1,2-双（苯基磺酰）乙烯获得。对此类醚的去保护方法也进行了研究。
• Carbohydrate-derived PSE acetals: controlled base-induced ring cleavage
  作者：Florence Chéry、Elena Cabianca、Arnaud Tatibouët、Ottorino De Lucchi、Patrick Rollin

  DOI：10.1016/j.tet.2011.11.009

  日期：2012.1

  Retro-Michael type reactions applied to PSE acetals protecting monosaccharides led either to complete removal or to ring-cleavage. In protic medium, application of standard basic conditions resulted in acetal deprotection, while the use of butyl lithium in aprotic medium allowed controlled ring-cleavage. A regio-and stereoselective C- over O-alkylation was observed during the process. Furthermore, depending on the substrates and the reaction conditions involved, new carbohydrate-derived beta-alkoxyvinyl sulfones were obtained with varying regioselectivity. (C) 2011 Elsevier Ltd. All rights reserved.