3-O-(2,4,6-tri-O-benzyl-3-deoxy-3-isobutylsulfonomethyl-β-D-galactopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol | 1236148-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2,4,6-tri-O-benzyl-3-deoxy-3-isobutylsulfonomethyl-β-D-galactopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol
• 英文别名: 2-methylpropyl [(2R,3R,4S,5R,6R)-2-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-hexadecoxypropoxy]-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]methanesulfonate
• CAS: 1236148-15-4
• 化学式: C₅₇H₉₂O₁₀SSi
• 分子量: 997.503
• InChiKey: AGHZCNCONRRMNQ-VGFZGGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.62
• 重原子数：
  69
• 可旋转键数：
  38
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-(2,4,6-tri-O-benzyl-3-deoxy-3-isobutylsulfonomethyl-β-D-galactopyranosyl)-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol 在 三氟乙酸 作用下， 反应 2.0h， 生成
  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：

  3-O-[2,4,6-tri-O-benzyl-3-deoxy-3-(E/Z)-isobutylsulfonomethylene-β-D-galactopyranosyl]-2-O-tert-butyldimethylsilyl-1-O-hexadecyl-sn-glycerol 在 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以85%的产率得到3-O-(2,4,6-tri-O-benzyl-3-deoxy-3-isobutylsulfonomethyl-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