3-((2R,3S,4S,5S,6R)-6-Allyl-4,5-bis-benzyloxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester | 794568-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((2R,3S,4S,5S,6R)-6-Allyl-4,5-bis-benzyloxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester
• 英文别名: ethyl 3-[(2R,3S,4S,5S,6R)-3-(2-methoxy-2-oxoethyl)-4,5-bis(phenylmethoxy)-6-prop-2-enyloxan-2-yl]propanoate
• CAS: 794568-35-7
• 化学式: C₃₀H₃₈O₇
• 分子量: 510.628
• InChiKey: MOIHICBFRADIDV-JLJIDRTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-((2R,3S,4S,5S,6R)-6-Allyl-4,5-bis-benzyloxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester 在 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以91%的产率得到3-[(2R,3S,4S,5S,6R)-4,5-Bis-benzyloxy-3-methoxycarbonylmethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propionic acid ethyl ester
  参考文献：
  名称：

  First Synthesis of a Branched β-C-Tetrasaccharide Using a Triple Ring Closing Metathesis Cyclization

  摘要：

  The first synthesis of a branched beta-C-tetrasaccharide has been carried out through the use of an esterification-ring closing metathesis (RCM) strategy. The precursor triacid 2a was readily prepared via standard chemical methods from a known starting material, and dehydrative coupling with an excess of olefin alcohol 1a gave triester 3a in excellent yield. Methylenation of the triester 3a and subsequent triple RCM reaction was followed by an in situ hydroboration-oxidation to furnish the branched beta-C-tetrasaccharide 6a in good overall yield.

  DOI：

  10.1021/jo040203w
• 作为产物：
  描述：

  烯丙基三甲基硅烷 、 3-((2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以93%的产率得到3-((2R,3S,4S,5S,6R)-6-Allyl-4,5-bis-benzyloxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  First Synthesis of a Branched β-C-Tetrasaccharide Using a Triple Ring Closing Metathesis Cyclization

  摘要：

  The first synthesis of a branched beta-C-tetrasaccharide has been carried out through the use of an esterification-ring closing metathesis (RCM) strategy. The precursor triacid 2a was readily prepared via standard chemical methods from a known starting material, and dehydrative coupling with an excess of olefin alcohol 1a gave triester 3a in excellent yield. Methylenation of the triester 3a and subsequent triple RCM reaction was followed by an in situ hydroboration-oxidation to furnish the branched beta-C-tetrasaccharide 6a in good overall yield.

  DOI：

  10.1021/jo040203w

文献信息

• First Synthesis of a Branched β-<i>C</i>-Tetrasaccharide Using a Triple Ring Closing Metathesis Cyclization
  作者：Jared L. Piper、Maarten H. D. Postema

  DOI：10.1021/jo040203w

  日期：2004.10.1

  The first synthesis of a branched beta-C-tetrasaccharide has been carried out through the use of an esterification-ring closing metathesis (RCM) strategy. The precursor triacid 2a was readily prepared via standard chemical methods from a known starting material, and dehydrative coupling with an excess of olefin alcohol 1a gave triester 3a in excellent yield. Methylenation of the triester 3a and subsequent triple RCM reaction was followed by an in situ hydroboration-oxidation to furnish the branched beta-C-tetrasaccharide 6a in good overall yield.