ChemInform Abstract: Efficient Synthesis of Optically Active β-Hydroxy p-Tolylsulfones with Very High Enantiomeric Excess via CBS-Oxazaborolidine-Catalyzed Borane Reduction.

ChemInform ◽  
2010 ◽  
Vol 33 (4) ◽  
pp. no-no
Author(s):  
Byung Tae Cho ◽  
Dong Jun Kim

ChemInform ◽  
2010 ◽  
Vol 31 (46) ◽  
pp. no-no ◽  
Author(s):  
J. S. Yadav ◽  
P. Thirupathi Reddy ◽  
S. Riaz Hashim


1990 ◽  
Vol 68 (1) ◽  
pp. 360-365 ◽  
Author(s):  
Shaukat Ali ◽  
Robert Bittman

A stereocontrolled route to 1-palmitoyl-2-O-hexadecyl-sn-glycero-3-phosphocholine from (R)-glycidyl tosylate is described. This method gives very high enantioselectivity (93–96% enantiomeric excess) and can be used to prepare 3-acyl-2-O-alkyl-sn-glycero-1-phosphocholines from (S)-glycidyl tosylate. The key step is the preparation of 1-O-benzyl-sn-glycerol 3-tosylate by the boron trifluoride etherate catalyzed regio- and stereo-specific opening of the epoxide ring with excess benzyl alcohol. The alkyl group is introduced using alkyl trifluoromethanesulfonate in the presence of excess 2,6-di-tert-butyl-4-methylpyridine. Debenzylation gives 2-O-alkyl-sn-glycerol 3-arenesulfonate, which is acylated and then converted into the phosphocholine. The use of chiral glycidyl derivatives as starting materials for the synthesis of glycerophospholipids is discussed.Key words: acylalkylglycerophospholipids, phospholipid synthesis, glycidyl derivatives in phospholipid synthesis, epoxides as precursors of phospholipids.



ChemInform ◽  
2005 ◽  
Vol 36 (8) ◽  
Author(s):  
J. S. Yadav ◽  
B. V. S. Reddy ◽  
G. Satheesh ◽  
P. Naga Lakshmi ◽  
S. Kiran Kumar ◽  
...  


Heterocycles ◽  
1992 ◽  
Vol 33 (2) ◽  
pp. 831 ◽  
Author(s):  
Seiichi Takano ◽  
Masashi Akiyama ◽  
Takumichi Sugihara ◽  
Kunio Ogasawara


ChemInform ◽  
2010 ◽  
Vol 23 (49) ◽  
pp. no-no
Author(s):  
S. TAKANO ◽  
M. AKIYAMA ◽  
T. SUGIHARA ◽  
K. OGASAWARA


Synthesis ◽  
1983 ◽  
Vol 1983 (08) ◽  
pp. 676-678 ◽  
Author(s):  
Jean-Alain Fehrentz ◽  
Bertrand Castro


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