pyridin-2-yl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside | 164923-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyridin-2-yl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-pyridin-2-ylsulfanyloxan-3-ol
• CAS: 164923-35-7
• 化学式: C₃₂H₃₃NO₅S
• 分子量: 543.684
• InChiKey: KASCLEJGHSBBNW-AQTFCTACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pyridin-2-yl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 samarium diiodide 、 环己酮 、 sodium hydride 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3,4,6-三苄氧基-D-葡萄烯糖
  参考文献：
  名称：

  A General Approach to 1,2-trans-C-Glycosides via Glycosyl Samarium(III) Compounds

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19980416)4:4<655::aid-chem655>3.3.co;2-w
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 potassium carbonate 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.0h， 生成 pyridin-2-yl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  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

• Efficient intramolecular β-mannoside formation using m-xylylene and isophthaloyl derivatives as rigid spacers
  作者：Adel A.-H. Abdel-Rahman、El Sayed H. El Ashry、Richard R. Schmidt

  DOI：10.1016/s0008-6215(01)00306-8

  日期：2002.2

  A series of mannosyl donors linked via position 2 to an m-xylylene or an isophthaloyl spacer which was connected to the position 6 of a glucoside acceptor afforded, via intramolecular glycosylation, the corresponding disaccharides with high beta anomeric ratio.

  一系列甘露糖基供体经由位置2连接至间二甲苯基或间苯二甲酰基间隔基，所述间二甲苯基或间苯二甲酰基间隔基连接至葡糖苷受体的位置6，通过分子内糖基化提供具有高β异头物比率的相应二糖。
• 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.
• A General Approach to 1,2-trans-C-Glycosides via Glycosyl Samarium(III) Compounds
  作者：Troels Skrydstrup、Olivier Jarreton、Daniel Mazéas、Dominique Urban、Jean-Marie Beau

  DOI：10.1002/(sici)1521-3765(19980416)4:4<655::aid-chem655>3.3.co;2-w

  日期：1998.4.16