Methyl 2,3-Di-O-benzyl-4,6-O-(2-phenylsulfonyl)ethylidene-α-D-mannopyranoside | 280557-35-9

• 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-phenylsulfonyl)ethylidene-α-D-mannopyranoside
• 英文别名: methyl 2,3-di-O-benzyl-4,6-O-(2-phenylsulphonyl)-ethylidene-α-D-mannopyranoside；(2R,4aR,6S,7S,8S,8aR)-2-(benzenesulfonylmethyl)-6-methoxy-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 280557-35-9
• 化学式: C₂₉H₃₂O₈S
• 分子量: 540.634
• InChiKey: ZAJBIJVVVZTBLB-VUTJFYCQSA-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-phenylsulfonyl)ethylidene-α-D-mannopyranoside 在 乙醇 、 potassium hydroxide 作用下， 反应 16.0h， 以65%的产率得到methyl 2,3-di-O-benzyl-α-D-mannopyranoside
  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：

  methyl 2,3-di-O-benzyl-α-D-mannopyranoside 、 1,2-bis(phenylsulfonyl)ethylene 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87%的产率得到Methyl 2,3-Di-O-benzyl-4,6-O-(2-phenylsulfonyl)ethylidene-α-D-mannopyranoside
  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

• Reductive opening of carbohydrate phenylsulfonylethylidene (PSE) acetals
  作者：Florence Chéry、Elena Cabianca、Arnaud Tatibouët、Ottorino De Lucchi、Thisbe K. Lindhorst、Patrick Rollin

  DOI：10.1016/j.carres.2015.09.011

  日期：2015.11

  carbohydrate-derived phenylsulfonylethylidene (PSE) acetals show a different behavior in reductive desulfonylation than simple symmetrical acetals. Here we have investigated various SET-type reaction conditions in order to open PSE acetals regioselectively and to produce chiral omega-hydroxyethenyl ethers. Whereas sodium amalgam leads to a mixture of regioisomeric vinyl ethers besides the ethylidene acetal, samarium

  苯磺酰基亚乙基（PSE）缩醛在碳水化合物化学中是一个相对较新的保护基。但是，碳水化合物衍生的苯磺酰亚乙基（PSE）缩醛在还原性脱磺酰基反应中的行为与简单的对称缩醛不同。在这里，我们研究了各种SET型反应条件，以选择性地打开PSE缩醛并生产手性ω-羟基乙烯基醚。汞齐除亚乙缩醛外还产生了区域异构乙烯基醚的混合物，而碘化for则适合于区域选择性的开环。用七个不同的碳水化合物PSE乙缩醛（分别为1,3-二氧杂环己烷和1,3-二氧戊环类型）显示。
• 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.
• 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.