[(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-triphenylphosphanium;iodide | 63599-65-5

• 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: [(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-triphenylphosphanium;iodide
• CAS: 63599-65-5
• 化学式: C₂₇H₃₀O₄P*I
• 分子量: 576.411
• InChiKey: QHUMFHYCVUBBNM-OECAZJPBSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl-triphenylphosphanium;iodide 在 palladium dihydroxide 正丁基锂 、 Amberlite IR 120 、 氢气 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 水 、 溶剂黄146 为溶剂， -50.0~85.0 ℃ 、800.0 kPa 条件下， 反应 19.0h， 生成 (3R,4S,5S)-5-[2-((2R,3R,4R,5S)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidin-2-yl)-ethyl]-tetrahydro-furan-2,3,4-triol; hydrochloride
  参考文献：
  名称：

  Convergent synthesis of pyrrolidine-based (1→6)- and (1→5)-aza-C-disaccharides

  摘要：

  A new entry to (1 --> 6)- and (1 --> 5)-aza-C-disaccharides featuring the pyrrolidine ring as the imino sugar component is described via Wittig condensation of polyhydroxylated 2-formylpyrrolidines with galactopyranose 6-phosphorane and ribofuranose 5-phosphorane, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01005-4

文献信息

• New Synthesis of Pyrrolidine Homoazasugars via Aminohomologation of Furanoses and Their Use for the Stereoselective Synthesis of Aza-<i>C</i>-disaccharides
  作者：Alessandro Dondoni、Pier Paolo Giovannini、Daniela Perrone

  DOI：10.1021/jo020252d

  日期：2002.10.1

  in 17% overall yields (six steps). The formyl aza-C-glycosides proved to be valuable intermediates for the synthesis of more complex derivatives. In fact, these sugar aldehydes were employed in Wittig-type coupling reactions with galactose and ribose phosphoranes to give bis-glycosylated alkenes, which upon reduction of the double bond were transformed into methylene isosteres of (1-->6)- and (1-->5)-linked

  通过2-N-硫代噻唑立体选择性加成到N-上，在2,3,5-三-O-苄基呋喃糖酶的异头异构体中心引入甲酰基并用碱性氮原子取代环氧（氨基同位）苄基，N-呋喃糖基羟胺（被掩盖的N-苄基糖硝酮），然后对所得的开链加合物进行还原性脱羟基反应，然后通过氨基上的游离羟基分子内置换并从甲酰基上除去甲酰基来进行闭环噻唑环。通过将甲酰基还原为羟甲基并通过氢解除去O-和N-苄基，将所得甲酰基氮杂-C-糖苷转化为2,5-二脱氧-2,5-亚氨基己糖醇（吡咯烷高氮杂）。 。将此反应序列应用于四种呋喃糖酶（D-阿拉伯糖，D-核糖，D-lyxo，L-xylo），以17％的总收率（六个步骤）得到无羟基和氨基的纯天竺葵，包括天然产物2,5-二脱氧-2,5-亚氨基-D-甘露醇。甲酰基氮杂-C-糖苷被证明是合成更复杂衍生物的有价值的中间体。实际上，这些糖醛与半乳糖和核糖磷烷一起用于Wittig型偶联反应中，生成双糖基化的烯烃，双键还原后转化为（1->
• Glycoside-Clustering Round Calixarenes toward the Development of Multivalent Carbohydrate Ligands. Synthesis and Conformational Analysis of Calix[4]arene <i>O</i>- and <i>C</i>-Glycoconjugates
  作者：Alessandro Dondoni、Martin Kleban、Xubo Hu、Alberto Marra、Harold D. Banks

  DOI：10.1021/jo020178z

  日期：2002.7.1

  and C-glycosyl calixarenes (calixsugars) have been prepared by tethering carbohydrate moieties to a tetrapropoxycalix[4]arene scaffold through alkyl chains. Two methodologies have been employed. One consisted of the stereoselective multiple glycosylation of upper rim calix[4]arene polyols leading to calix-O-glycosides; the other involved a multiple Wittig olefination of upper rim calix[4]arene-derived

  通过将碳水化合物部分通过烷基链束缚到四丙氧基杯[4]芳烃骨架上，制备了双-和四-O-和C-糖基杯芳烃（杯糖）。已经采用了两种方法。一种是由上边缘杯[4]芳烃多元醇的立体选择性多重糖基化反应而形成杯-O-糖苷。另一种涉及通过使用糖磷烷将上边缘杯[4]芳烃衍生的多醛进行多次维蒂希烯烃化反应，并还原烯烃双键，得到杯-C-糖苷。双糖基化产物的NMR光谱和NOE实验表明，带有糖保护残基的化合物优先以扁平圆锥排列形式（远构象）存在于溶液中，而脱保护的衍生物则采用紧密构象。
• The assembly of carbon-linked calixarene-carbohydrate structures (C-calixsugars) by multiple wittig olefination
  作者：Alessandro Dondoni、Martin Kleban、Alberto Marra

  DOI：10.1016/s0040-4039(97)10041-7

  日期：1997.11

  The Wittig olefination of the O-propyl tetraformylcalix[4]arene 1 with sugar phosphoranes and reduction of the resulting alkenes lead to calixarene derivatives holding three and four carbohydrate units through an ethylene linkage (C-calixsugars). (C) 1997 Elsevier Science Ltd.
• Convergent synthesis of pyrrolidine-based (1→6)- and (1→5)-aza-C-disaccharides
  作者：Alessandro Dondoni、Pier Paolo Giovannini、Alberto Marra

  DOI：10.1016/s0040-4039(00)01005-4

  日期：2000.8

  A new entry to (1 --> 6)- and (1 --> 5)-aza-C-disaccharides featuring the pyrrolidine ring as the imino sugar component is described via Wittig condensation of polyhydroxylated 2-formylpyrrolidines with galactopyranose 6-phosphorane and ribofuranose 5-phosphorane, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.