4,6-di-O-benzyl-3-O-triisopropylsilyl-D-galactal

• 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: 4,6-di-O-benzyl-3-O-triisopropylsilyl-D-galactal
• 英文别名: [(2R,3S,4R)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy-tri(propan-2-yl)silane
• 化学式: C₂₉H₄₂O₄Si
• 分子量: 482.736
• InChiKey: IGRNDDRGXFZDTH-MPFGFTFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 4,6-di-O-benzyl-3-O-triisopropylsilyl-D-galactal 在 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以68%的产率得到[(2R,3S,4R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-4-yloxy]-triisopropyl-silane
  参考文献：
  名称：

  Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides

  摘要：

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.

  DOI：

  10.1021/ja031895t
• 作为产物：
  描述：

  三异丙基氯硅烷 、 4,6-di-O-benzyl-D-galactal 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以92%的产率得到4,6-di-O-benzyl-3-O-triisopropylsilyl-D-galactal
  参考文献：
  名称：

  Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides

  摘要：

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.

  DOI：

  10.1021/ja031895t

文献信息

• Rhenium(V)-Catalyzed Synthesis of 2-Deoxy-α-glycosides
  作者：Benjamin D. Sherry、Rebecca N. Loy、F. Dean Toste

  DOI：10.1021/ja031895t

  日期：2004.4.1

  A mild method for the synthesis of 2-deoxysugars from the coupling of glycals with a range of nucleophiles is described. The method employs 1 mol % of an air- and moisture-tolerant rhenium-oxo complex [ReOCl3(SMe2)(Ph3PO)] as a catalyst for the formation of O-, N-, and S-alpha-glycosides. The catalytic system tolerates a number of commonly employed protecting groups, including isopropylidene acetals, alkyl and silyl ethers, acetates, and benzoates. Furthermore, the high-oxidation-state complex selectively catalyzes the coupling with the glycal acceptor in preference to oxidation of the glycals, alcohols, and even thiols.