(2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-octyl-tetrahydro-pyran-3,4,5-triol | 79537-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-octyl-tetrahydro-pyran-3,4,5-triol
• 英文别名: (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-octyloxane-3,4,5-triol
• CAS: 79537-23-8
• 化学式: C₁₄H₂₈O₅
• 分子量: 276.373
• InChiKey: ZDQIZHVGQJZVOZ-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-octyl-tetrahydro-pyran-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 Tetra-O-acetyl-α-C-octylglucosid
  参考文献：
  名称：

  1,2-cis-C-glycoside synthesis by samarium diiodide-promoted radical cyclizations

  摘要：

  AbstractThe samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon‐tethered unsaturated group at the C2–OH position leads to the stereo‐specific synthesis of 1,2‐cis‐C‐glycosides in good yield after desilylation. These reactions proceed via an anomeric radical with subsequent 5‐exo cyclization. Unlike the corresponding glycosyl phenyl sulfones, the pyridyl derivatives react instantaneously with samarium diiodide and do not require a cosolvent such as hexamethylphosphoramide (HMPA). Under these reaction conditions radical cyclization precedes the second reduction step. Examples of 5‐exo‐trig and ‐dig ring closures are given. The synthetic utility of this method was demonstrated by a short synthesis of methyl C‐isomaltoside.

  DOI：

  10.1002/chem.19970030822
• 作为产物：
  描述：

  2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl 2-pyridyl sulfone 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-octyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  1,2-cis-C-glycoside synthesis by samarium diiodide-promoted radical cyclizations

  摘要：

  AbstractThe samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon‐tethered unsaturated group at the C2–OH position leads to the stereo‐specific synthesis of 1,2‐cis‐C‐glycosides in good yield after desilylation. These reactions proceed via an anomeric radical with subsequent 5‐exo cyclization. Unlike the corresponding glycosyl phenyl sulfones, the pyridyl derivatives react instantaneously with samarium diiodide and do not require a cosolvent such as hexamethylphosphoramide (HMPA). Under these reaction conditions radical cyclization precedes the second reduction step. Examples of 5‐exo‐trig and ‐dig ring closures are given. The synthetic utility of this method was demonstrated by a short synthesis of methyl C‐isomaltoside.

  DOI：

  10.1002/chem.19970030822

文献信息

• 1,2-cis-C-glycoside synthesis by samarium diiodide-promoted radical cyclizations
  作者：Troels Skrydstrup、Daniel Mazéas、Mohamed Elmouchir、Gilles Doisneau、Claude Riche、Angèle Chiaroni、Jean-Marie Beau

  DOI：10.1002/chem.19970030822

  日期：1997.8

  AbstractThe samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon‐tethered unsaturated group at the C2–OH position leads to the stereo‐specific synthesis of 1,2‐cis‐C‐glycosides in good yield after desilylation. These reactions proceed via an anomeric radical with subsequent 5‐exo cyclization. Unlike the corresponding glycosyl phenyl sulfones, the pyridyl derivatives react instantaneously with samarium diiodide and do not require a cosolvent such as hexamethylphosphoramide (HMPA). Under these reaction conditions radical cyclization precedes the second reduction step. Examples of 5‐exo‐trig and ‐dig ring closures are given. The synthetic utility of this method was demonstrated by a short synthesis of methyl C‐isomaltoside.