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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 5-6
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Original Articles

Synthesis of 2, 3-dideoxy-4-O-p-methoxybenzyl-L-erythro-hex-2-enono-1, 5-lactone

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Pages 1025-1037 | Received 27 Sep 1988, Published online: 24 Oct 2006

References

  • Marco , J. L. and Hueso-Rodríguez , J. A. 1988 . Tetrahedron Lett. , 29 : 2459
  • Otera , J. 1988 . Synthesis , : 95
  • Alemany , A. , Marquez , C. , Pascual , C. , Valverde , S. , Perales , A. , Fayos , J. and Martínez-Ripoll , M. 1979 . Tetrahedron Lett. , 3579 : 3583
  • Kennedy , J. F. and White , C. A. 1983 . Bioactive Carbohydrates , Chichester, , U. K. : Ellis Horwood Publishers .
  • Valverde , S. , Herradón , B. and Martí-Lomas , M. 1985 . Tetrahedron Lett. , 26 : 3731 Recently, the synthesis of 4-O-benzyl-2, 3-dideoxy-L-threo-hex-2-enono-1, 5-lactone, an analogue of 9, from dimethyl-L-tartrate, has been reported:
  • Lok , C. M. , Ward , J. P. and van Dorp , D. A. 1976 . Chem. Phys. Lipids , 16 : 115
  • Larchevěque , M. and Petit , Y. 1986 . Synthesis , : 60
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  • Oikawa , Y. , Yosioka , T. and Yonemitsu , O. 1982 . Tetrahedron Lett. , 23 : 885
  • Czernecki , S. , Georgulis , C. and Provelenghion , C. 1976 . Tetrahedron Lett. , : 3535
  • It is interesting to note that, in our hands, the silver nitrate/1, 4-diazabicyclo[2. 2. 2]octane method (see ref. 8) gave the best results (ref. 2).
  • Still , W. C. , Kahn , M. and Mitra , A. 1978 . J. Org. Chem. , 43 : 2923
  • We could not obtain pure the minor 7 syn isomer, which was contaminated with traces of 7 anti.
  • Tronchet , J. M. and Gentile , B. 1971 . Helv. Chim. Acta. , 62 : 2091

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