Rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1- O-alkyl-2-desoxy-2-amino- sn-glycero-3-phosphocholines, -3-phospho- N, N′-dimethylethanolamine and -3-phospho-Fmoc-serine-methylester
A convenient sequence for the rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1- O-alkyl-2-amino-2-desoxy-3-phospho- derivatives is described. Key steps are the reaction of 1-carbonyloxyalkyl-, 1-alkyl- or 1- O-alkyl-amino-alcohols with phosphor...
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Published in | Chemistry and physics of lipids Vol. 61; no. 2; pp. 199 - 208 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
Shannon
Elsevier Ireland Ltd
01.04.1992
Elsevier Science |
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Abstract | A convenient sequence for the rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1-
O-alkyl-2-amino-2-desoxy-3-phospho- derivatives is described. Key steps are the reaction of 1-carbonyloxyalkyl-, 1-alkyl- or 1-
O-alkyl-amino-alcohols with phosphorus oxychloride to 1-carbonyloxyalkyl-, 1-alkyl- or 4-substituted 2-chloro-2-oxo-1,3,2-oxazaphospholane followed by nucleophilic displacement with choline tosylate, 1-bromoethane-2-ol or Fmoc-
l-serine-methylester and subsequent hydrolysis to 2-amino-lysophospholipids giving the desired compounds in yields ranging between 68% and 81%. Several 2-amino-lysophospholipid analogs can then be prepared by this synthetic scheme utilizing the same oxazaphospholane intermediate. A brief method for the preparation of 2-amino-3-hydroxy-propionic-acid-pentyl- and -octylester from
l-serine is described, opening a facile access to chiral precursors of phospholipid analogs. |
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AbstractList | A convenient sequence for the rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1-
O-alkyl-2-amino-2-desoxy-3-phospho- derivatives is described. Key steps are the reaction of 1-carbonyloxyalkyl-, 1-alkyl- or 1-
O-alkyl-amino-alcohols with phosphorus oxychloride to 1-carbonyloxyalkyl-, 1-alkyl- or 4-substituted 2-chloro-2-oxo-1,3,2-oxazaphospholane followed by nucleophilic displacement with choline tosylate, 1-bromoethane-2-ol or Fmoc-
l-serine-methylester and subsequent hydrolysis to 2-amino-lysophospholipids giving the desired compounds in yields ranging between 68% and 81%. Several 2-amino-lysophospholipid analogs can then be prepared by this synthetic scheme utilizing the same oxazaphospholane intermediate. A brief method for the preparation of 2-amino-3-hydroxy-propionic-acid-pentyl- and -octylester from
l-serine is described, opening a facile access to chiral precursors of phospholipid analogs. A convenient sequence for the rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester , 1-alkyl-1-desoxy- and 1-O-alkyl-2-amino-2-desoxy-3-phospho-derivatives is described. Key steps are the reaction of 1-carbonyloxyalkyl-, 1-alkyl- or 1-O-alkyl-amino-alcohols with phosphorus oxychloride to 1-carbonyloxyalkyl-, 1-alkyl- or 4-substituted 2-chloro-2-oxo-1,3,2-oxazaphospholane followed by nucleophilic displacement with choline tosylate, 1-bromoethane-2-ol or Fmoc-L-serine-methylester and subsequent hydrolysis to 2-amino-lysophospholipids giving the desired compounds in yields ranging between 68% and 81%. Several 2-amino-lysophospholipid analogs can then be prepared by this synthetic scheme utilizing the same oxazaphospholane intermediate. A brief method for the preparation of 2-amino-3-hydroxy-propionic-acid-pentyl- and -octylester from L-serine is described, opening a facile access to chiral precursors of phospholipid analogs. |
Author | Deigner, Hans-Peter Fyrnys, Beatrix |
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Cites_doi | 10.1016/0005-2760(90)90111-A 10.1016/0005-2760(90)90110-J 10.1007/BF02533575 10.1016/0005-2760(90)90112-B 10.1002/hlca.19580410640 10.1021/jo00156a011 10.1016/0005-2760(90)90238-S 10.1038/347689a0 10.1042/bst0170274 |
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Keywords | 2-amino-lysophospholipid analogs phospholipid 2-desoxy-2-amino- sn-glycerophospholipids ether lipid Phosphatidylcholine Phospholipid Aminoether Complex lipid Analog |
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References | Dijkman, Dekker, de Haas (BIB1) 1990; 1043 Guttman, Boissonnas (BIB8) 1958; 41 Thunissen, Ab, Kalk, Drenth, Dijkstra, Kuipers, Dijkstra, de Haas, Verheij (BIB4) 1990; 347 Ransac, Rivière, Soulié, Gancet, Verger, de Haas (BIB2) 1990; 1043 de Haas, Dijkman, van Oort, Verger (BIB3) 1990; 1043 Eibl (BIB9) 1978; 75 Brockerhoff, Ayengar (BIB7) 1979; 14 Chandrakumar, Hajdu (BIB6) 1983; 48 de Haas, Dijkman, Ransac, Verger (BIB5) 1990; 1046 de Haas, van Oort, Dijkman, Verger (BIB10) 1989; 17 de Haas (10.1016/0009-3084(92)90013-F_BIB3) 1990; 1043 Eibl (10.1016/0009-3084(92)90013-F_BIB9) 1978; 75 de Haas (10.1016/0009-3084(92)90013-F_BIB5) 1990; 1046 Brockerhoff (10.1016/0009-3084(92)90013-F_BIB7) 1979; 14 de Haas (10.1016/0009-3084(92)90013-F_BIB10) 1989; 17 Ransac (10.1016/0009-3084(92)90013-F_BIB2) 1990; 1043 Thunissen (10.1016/0009-3084(92)90013-F_BIB4) 1990; 347 Chandrakumar (10.1016/0009-3084(92)90013-F_BIB6) 1983; 48 Guttman (10.1016/0009-3084(92)90013-F_BIB8) 1958; 41 Dijkman (10.1016/0009-3084(92)90013-F_BIB1) 1990; 1043 |
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Snippet | A convenient sequence for the rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1-... A convenient sequence for the rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester , 1-alkyl-1-desoxy- and... |
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SubjectTerms | 2-amino-lysophospholipid analogs 2-desoxy-2-amino- sn-glycerophospholipids Chemistry ether lipid Exact sciences and technology Lipids Magnetic Resonance Spectroscopy Methods Molecular Structure Organic chemistry Phospholipases - antagonists & inhibitors phospholipid Phospholipids - chemical synthesis Phospholipids - chemistry Phospholipids - pharmacology Preparations and properties Spectrometry, Mass, Fast Atom Bombardment |
Title | Rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1- O-alkyl-2-desoxy-2-amino- sn-glycero-3-phosphocholines, -3-phospho- N, N′-dimethylethanolamine and -3-phospho-Fmoc-serine-methylester |
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