methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulphonyl)-ethylidene-α-D-glucopyranoside | 280557-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulphonyl)-ethylidene-α-D-glucopyranoside
• 英文别名: Methyl 2,3-Di-O-benzyl-4,6-O-(2-phenylsulfonyl)ethylidene-α-D-glucopyranoside；(2R,4aR,6S,7R,8S,8aR)-2-(benzenesulfonylmethyl)-6-methoxy-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 280557-34-8
• 化学式: C₂₉H₃₂O₈S
• 分子量: 540.634
• InChiKey: ZAJBIJVVVZTBLB-CJSXUKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulphonyl)-ethylidene-α-D-glucopyranoside 在 三氟乙酸 作用下， 反应 2.0h， 以82%的产率得到Methyl 4,6-O-(2-phenylsulfonyl)ethylidene-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  1,2-bis(phenylsulfonyl)ethylene 、 2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 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99%的产率得到methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulphonyl)-ethylidene-α-D-glucopyranoside
  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

• Regioselective de-O-benzylation of phenylsulfonylethylidene (PSE) acetals-containing benzylated monosaccharides using triisobutylaluminum (TIBAL)
  作者：Bérengère Chevalier-du Roizel、Elena Cabianca、Patrick Rollin、Pierre Sinaÿ

  DOI：10.1016/s0040-4020(02)01249-8

  日期：2002.11

  A series of benzylated monosaccharidic PSE acetals undergoes regioselective TIBAL-mediated de-O-benzylation, to afford monobenzyl ethers, readily available as building blocks for oligosaccharides synthesis.

  一系列苄基化的单糖化PSE缩醛经过区域选择性TIBAL介导的去-O-苄基化反应，得到单苄基醚，很容易用作寡糖合成的基础。
• 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.
• 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.
• Cabianca; Tatibouet; Rollin, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 317 - 322
  作者：Cabianca、Tatibouet、Rollin

  DOI：——

  日期：——
• 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。