6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal | 1033614-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal
• CAS: 1033614-33-3
• 化学式: C₂₆H₄₀O₉SSi
• 分子量: 556.75
• InChiKey: FRQSRUWHDZXBJB-CRNSPECLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 6-O-[6'-O-(benzyl)-2',3'-dideoxy-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-D-glucal
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3-Unsaturated 1,6-Oligosaccharides by Means of a Glycal-Derived Allyl Epoxide and N-Nosyl Aziridine

  摘要：

  beta-D-threo- and 4-deoxy-4-amino-alpha-D-erythro-hex-2-enopyranosyl di- (n = 0) and trisaccharides (n = 1) of types A and B were synthetized by means of a reiterative, completely stereoselective glycosylation process which makes use of the D-galactal-derived allyl epoxide 1 beta and D-allal-derived allyl N-nosyl aziridine 2 alpha, respectively.

  DOI：

  10.1021/ol800793f
• 作为产物：
  描述：

  3-O-(t-butyldimethylsilyl)-4-O-mesyl-D-glucal 、 6-O-(benzyl)-4-O-mesyl-D-glucal 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 以72%的产率得到6-O-[6'-O-(benzyl)-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl]-4-O-mesyl-3-O-(t-butyldimethylsilyl)-D-glucal
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3-Unsaturated 1,6-Oligosaccharides by Means of a Glycal-Derived Allyl Epoxide and N-Nosyl Aziridine

  摘要：

  beta-D-threo- and 4-deoxy-4-amino-alpha-D-erythro-hex-2-enopyranosyl di- (n = 0) and trisaccharides (n = 1) of types A and B were synthetized by means of a reiterative, completely stereoselective glycosylation process which makes use of the D-galactal-derived allyl epoxide 1 beta and D-allal-derived allyl N-nosyl aziridine 2 alpha, respectively.

  DOI：

  10.1021/ol800793f