2,2'-O-methylene-bis-(3-O-trityl-sn-glycerol) | 71769-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,2'-O-methylene-bis-(3-O-trityl-sn-glycerol)
• 英文别名: formaldehyde-[bis-((R)-β-hydroxy-β'-trityloxy-isopropyl)-acetal]；Formaldehyd-[bis-((R)-β-hydroxy-β'-trityloxy-isopropyl)-acetal]
• CAS: 71769-25-0
• 化学式: C₄₅H₄₄O₆
• 分子量: 680.841
• InChiKey: XEVNALTYDLQBMY-OCQXTOTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  51.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2'-O-methylene-bis-(3-O-trityl-sn-glycerol) 、 12-((tert-butoxycarbonyl)amino)dodecyl methanesulfonate 在 sodium hydride 作用下， 生成
  参考文献：
  名称：

  Synthesis of 1-O-alkyl-sn-glycerols and fluorescently labeled analogs from as precursor

  摘要：

  A new approach employing 2,5-O-methylene-D-Mannitol as precursor for the synthesis of naturally occurring and fluorescently labeled alkyl glycerols is described. From 2,5-O-methylene-D-mannitol, which was prepared according to the method of Ness et al. [1], 2,2-O-methylene-bis-(3-O-trityl)-sn-glycerol, the central product, was synthesized to an enantiomerically pure molecule in four steps. 1-O-hexadecyl-sn-glycerol was prepared by condensation of hexadecyl methanesulfonate with the central product and by subsequent detritylation and cleavage of the methylene bridge. From the alkyl glycerol the different lipid classes can be synthesized by well known strategies. To form fluorescently labeled analogs of alkyl glycerols the fluorescence marker 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) was linked with the omega-amino group of 1-O-(12-aminododecyl)-sn-glycerol. Therefore the central product was condensed with 12-N-t-BOC-aminododecyl methanesulfonate. The methylene bridge. the trityl groups and the BOC protection group were cleaved with boron trifluoride/methanol in one step. 1-O-(12-NBD-aminododecyl)-sn-glycerol is useful as a biochemical substrate to build up fluorescently labeled neutral lipids and phospholipids.

  DOI：

  10.1016/0009-3084(93)90036-3
• 作为产物：
  描述：

  O¹,O⁶-dibenzoyl-O²,O⁵-methanediyl-D-mannitol 在 吡啶 、 lead(IV) acetate 、 乙酸乙酯 作用下， 生成 2,2'-O-methylene-bis-(3-O-trityl-sn-glycerol)
  参考文献：
  名称：

  Wickberg, Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 1187,1195

  摘要：

  DOI：