3-[(2R,3S,4S,5S,6R)-3,6-bis(carboxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]propanoic acid | 794568-38-0

• 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)-3,6-bis(carboxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]propanoic acid
• CAS: 794568-38-0
• 化学式: C₂₆H₃₀O₉
• 分子量: 486.519
• InChiKey: LBLIMNJFMOGDFV-GBGUOAHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 、 3-[(2R,3S,4S,5S,6R)-3,6-bis(carboxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]propanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl] 3-[(2R,3S,4S,5S,6R)-3,6-bis[2-oxo-2-[(2R,3S,4R)-1,3,4-tris(phenylmethoxy)hex-5-en-2-yl]oxyethyl]-4,5-bis(phenylmethoxy)oxan-2-yl]propanoate
  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：

  3-((2R,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-propionic acid ethyl ester 在 lithium hydroxide 、 sodium chlorite 、 sodium periodate 、 potassium dihydrogenphosphate 、 四氧化锇 、 2-甲基-2-丁烯 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 21.0h， 生成 3-[(2R,3S,4S,5S,6R)-3,6-bis(carboxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]propanoic acid
  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.