(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran | 686341-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran
• CAS: 686341-48-0
• 化学式: C₄₇H₅₀O₈
• 分子量: 742.909
• InChiKey: WCPXHZSLOQYPBI-WLDPSFHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  55.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-thio-α-D-glucopyranoside 、 (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran 在 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以74%的产率得到[(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：

  3,4,6-三邻苄基半乳醛 在 [ReOCl3(OPPh3)(SMe2)] 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 35.5h， 生成 (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran
  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