66322-35-8Relevant academic research and scientific papers
Synthesis and chemical transformations of 4-hexadecyloxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane
Malekin,Khromova,Kisin,Kruglyak,Kurochkin
, p. 677 - 682 (2007/10/03)
Cyclophosphorylation of 1-hexadecylglycerol with phosphorus oxychloride afforded 4-hexadecyl-oxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane (I) with high yield. By means of 1H, 13C, and 31P NMR, it was shown to be a 1 : 9 mixture of two stable epimers with equatorial and axial configuration of the chlorine atom, respectively. Phospholane (I) entered into nucleophilic reactions with KHCO3 and HN(Pri)2 to give 80-85% yields of the chlorine substitution products with the phospholane cycle remaining intact. Interaction of the phospholane (I) with water or choline tosylate also initially produced substituted phospholanes, as shown by NMR. Subsequent hydrolysis led to the cleavage of the phospholane ring and to formation of isomeric 1-hexadecylglycero-2- and 3-phosphates and 1-hexadecylglycero-2- and 3-phosphocholines, respectively. A method for the separation of isomeric phosphates was developed, which made it possible to isolate 1-hexadecylglycero-2-phosphate and 1-hexadecylglycero-3-phosphate.
