1,2,5,6-tetra-palmitoyl-D-mannitol | 34767-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,5,6-tetra-palmitoyl-D-mannitol
• 英文别名: 1,2,5,6-Tetrapalmitoyl-D-mannitol；[(2R,3S,4S,5R)-2,5,6-tri(hexadecanoyloxy)-3,4-dihydroxyhexyl] hexadecanoate
• CAS: 34767-69-6
• 化学式: C₇₀H₁₃₄O₁₀
• 分子量: 1135.83
• InChiKey: YEVPRUZFWORQKE-XGTHTWCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28
• 重原子数：
  80
• 可旋转键数：
  69
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,2,5,6-tetra-palmitoyl-D-mannitol 、 Diisopropyl-phosphoramidous acid 2-chloro-ethyl ester 2-cyano-ethyl ester 在 四氮唑 、 双氧水 作用下， 生成 Hexadecanoic acid (1R,2R,3R,4R)-2,3-bis-[(2-chloro-ethoxy)-(2-cyano-ethoxy)-phosphoryloxy]-4,5-bis-hexadecanoyloxy-1-hexadecanoyloxymethyl-pentyl ester
  参考文献：
  名称：

  Synthesis and properties of new bisphosphatidylcholine lipids

  摘要：

  报道了利用磷酰胺偶联法合成新型双磷脂酰胆碱脂类物质的研究。

  DOI：

  10.1039/c39940002043
• 作为产物：
  描述：

  3,4-di-O-isopropylidene-D-mannitol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,5,6-tetra-palmitoyl-D-mannitol
  参考文献：
  名称：

  Synthesis and properties of new bisphosphatidylcholine lipids

  摘要：

  报道了利用磷酰胺偶联法合成新型双磷脂酰胆碱脂类物质的研究。

  DOI：

  10.1039/c39940002043

文献信息

• Process for preparing 1,2-diacyl-sn-glycerols
  申请人：KSV-Chemicals Oy

  公开号：US04360694A1

  公开（公告）日：1982-11-23

  The object of the present invention is a novel and simple process for the production of 1,2-diacyl-sn-glycerols, wherein the acyl groups may be the same or different. According to the invention D-mannitol is reacted with benzene boronic acid or a derivative thereof to form a D-mannitol-monobenzeneboronate which compound is acylated either to form, after removal of the benzeneboronate protective group, a 1,2,5,6-tetraacyl-D-mannitol with four identical acyl groups, or is acylated selectively in two stages, by first acylating the 1,6-hydroxy groups of the boronate protected D-mannitol to form, after removal of the boronate protection, a 1,6-diacyl-D-mannitol, which then is repeatedly reacted with a benzene boronic acid or a derivative thereof and then acylated in the 2- and 5-positions. After removal of the boronate protective group, the tetra-acylated D-mannitol obtained either in the one-stage or two-stage process is split by oxidation to form a 1,2-diacyl-glyceraldehyde which in turn is reduced to the corresponding 1,2-diacyl-sn-glycerol. By means of the invention it is thus possible to prepare 1,2-diacyl-sn-glycerols in which the acyl groups can be the same or different.

  本发明的目标是一种新颖且简单的生产1,2-二酰基-sn-甘油的方法，其中酰基可以相同或不同。根据本发明，D-甘露醇与苯基硼酸或其衍生物反应，形成D-甘露醇-单苯基硼酸酯，该化合物被酰化，形成去除苯基硼酸保护基后的1,2,5,6-四酰基-D-甘露醇，具有四个相同的酰基，或者被选择性地分两个阶段酰化，首先酰化硼酸保护的D-甘露醇的1,6-羟基，形成去除硼酸保护后的1,6-二酰基-D-甘露醇，然后反复与苯基硼酸或其衍生物反应，并在2-和5-位置酰化。去除硼酸保护基后，通过氧化将一阶段或两阶段过程中获得的四酰基D-甘露醇分解成1,2-二酰基甘油醛，然后还原为相应的1,2-二酰基-sn-甘油。通过本发明，因此可以制备出酰基可以相同或不同的1,2-二酰基-sn-甘油。
• Process for preparing 1,2-diacyl-SN-glycerols
  申请人：KSV-Chemicals Oy

  公开号：EP0037582A2

  公开（公告）日：1981-10-14

  The object of the present invention is a novel and simple process forthe production of 1,2-diacyl-sn-glycerols, wherein the acyl groups may be the same or different. According to the invention D-mannitol is reacted with benzene boronic acid or a derivative thereof to form a D-mannitol- monobenzeneboronate which compound is acylated either to form, after removal of the benzeneboronate protective group, a 1,2,5,6-tetraacyl-D-mannitol with four identical acyl groups, or is acylated selectively in two stages, by first acylating the 1,6-hydroxy groups of the boronate protected D-mannitol to form, after removal of the boronate protection, a 1,6-diacyl-D-mannitol, which then is repeatedly reacted with a benzene boronic acid or a derivative thereof and then acylated in the 2-and 5-positions. After removal of the boronate protective group, the tetra-acylated D-mannitol obtained either in the one-stage or two-stage process is split by oxidation to form a 1,2-diacyl-glyceraldehyde which in turn is reduced to the corresponding 1,2-diacyl-sn-glycerol. By means of the invention it is thus possible to prepare 1,2-diacyl-sn-glycerols in which the acyl groups can be the same or different.

  本发明的目的是一种生产 1,2-二乙酰基-sn-甘油的新颖而简单的工艺，其中的酰基可以是相同的，也可以是不同的。根据本发明，D-甘露醇与苯硼酸或其衍生物反应生成 D-甘露醇-单苯硼酸酯，该化合物经酰化后，在除去苯硼酸酯保护基后，形成具有四个相同酰基的 1，2，5，6-四酰基-D-甘露醇、或者选择性地分两个阶段酰化，首先酰化受硼酸酯保护的 D-甘露醇的 1，6-羟基，在去除硼酸酯保护基后形成 1，6-二酰基-D-甘露醇，然后与苯硼酸或其衍生物反复反应，再在 2 和 5 位酰化。除去硼酸保护基后，在一步法或两步法中得到的四酰化 D-甘露醇通过氧化作用分裂成 1,2-二乙酰基甘油醛，再还原成相应的 1,2-二乙酰基-sn-甘油。通过本发明，可以制备出酰基可以相同或不同的 1,2-二乙酰基-sn-甘油。
• Shvets,V.I. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 2175 - 2181
  作者：Shvets,V.I. et al.

  DOI：——

  日期：——
• US4360694A
  申请人：——

  公开号：US4360694A

  公开（公告）日：1982-11-23
• Synthesis and properties of new bisphosphatidylcholine lipids
  作者：Philippe Klotz、Louis A. Cuccia、Nazim Mohamed、George Just、R. Bruce Lennox

  DOI：10.1039/c39940002043

  日期：——

  The synthesis of novel bisphosphatidylcholine lipids using a phosphoramidite coupling scheme is reported.

  报道了利用磷酰胺偶联法合成新型双磷脂酰胆碱脂类物质的研究。