Acetic acid (2R,3S,4R)-2-acetoxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-4-yl ester | 686341-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R)-2-acetoxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-4-yl ester
• CAS: 686341-46-8
• 化学式: C₃₇H₄₂O₁₀
• 分子量: 646.734
• InChiKey: JCRZXPPDUCOLDW-JBRKAADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R)-2-acetoxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-4-yl ester 在 [ReOCl3(OPPh3)(SMe2)] 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 31.5h， 生成 [(2S,3S,4S,5R,6S)-4,5-dibenzoyloxy-2-[[(2R,4R,5S,6R)-5-[(2R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]sulfanylmethyl]-6-methoxyoxan-3-yl] benzoate
  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：

  3,6-di-O-acetyl-D-glucal 、 3,4,6-三邻苄基半乳醛 在 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以92%的产率得到Acetic acid (2R,3S,4R)-2-acetoxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-4-yl ester
  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