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 |
Subjects | |
Online Access | Get full text |
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Summary: | 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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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0009-3084 1873-2941 |
DOI: | 10.1016/0009-3084(92)90013-F |