3-O-(2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol | 1236148-10-9

• 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: 3-O-(2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol
• 英文别名: (2R,3S,5S,6R)-2-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-hexadecoxypropoxy]-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-one
• CAS: 1236148-10-9
• 化学式: C₅₂H₈₀O₈Si
• 分子量: 861.288
• InChiKey: UILPIPRBACBKCD-CCAXLNDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.57
• 重原子数：
  61
• 可旋转键数：
  33
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isobutyl (diethoxyphosphoryl)methanesulfonate 、 3-O-(2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 3-O-[2,4,6-tri-O-benzyl-3-deoxy-3-(Z)-isobutylsulfonomethylene-β-D-galactopyranosyl]-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol 、 3-O-[2,4,6-tri-O-benzyl-3-deoxy-3-(E)-isobutylsulfonomethylene-β-D-galactopyranosyl]-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of the Sulfonate Analogue of Seminolipid via Horner−Wadsworth−Emmons Olefination

  摘要：

  The first synthesis of the sulfonate analogue of seminolipid, the main sulfoglycolipid in mammalian sperm, is reported. Installation of the sulfonate unit was accomplished by a quite unexplored strategy based on Horner-Wadsworth-Emmons olefination on a 3'-keto-galactoside, followed by stereoselective double bond reduction.

  DOI：

  10.1021/jo1008788
• 作为产物：
  描述：

  在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以0.36 g的产率得到3-O-(2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of the Sulfonate Analogue of Seminolipid via Horner−Wadsworth−Emmons Olefination

  摘要：

  The first synthesis of the sulfonate analogue of seminolipid, the main sulfoglycolipid in mammalian sperm, is reported. Installation of the sulfonate unit was accomplished by a quite unexplored strategy based on Horner-Wadsworth-Emmons olefination on a 3'-keto-galactoside, followed by stereoselective double bond reduction.

  DOI：

  10.1021/jo1008788

文献信息

• Synthesis of the Sulfonate Analogue of Seminolipid via Horner−Wadsworth−Emmons Olefination
  作者：Laura Franchini、Federica Compostella、Diego Colombo、Luigi Panza、Fiamma Ronchetti

  DOI：10.1021/jo1008788

  日期：2010.8.6

  The first synthesis of the sulfonate analogue of seminolipid, the main sulfoglycolipid in mammalian sperm, is reported. Installation of the sulfonate unit was accomplished by a quite unexplored strategy based on Horner-Wadsworth-Emmons olefination on a 3'-keto-galactoside, followed by stereoselective double bond reduction.