Tetrahedron: Asymmetry

(−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications

FW Lichtenthaler, J Klotz, K Nakamura

Index: Lichtenthaler, Frieder W.; Klotz, Juergen; Nakamura, Katsumi Tetrahedron Asymmetry, 2003 , vol. 14, # 24 p. 3973 - 3986

Full Text: HTML

Citation Number: 11

Abstract

The dimethyl esters of the 2, 6-anhydro-3-deoxy-hept-2-enaric acids with d-xylo, d-lyxo, l- arabino, l-lyxo-and d-ribo-configuration were synthesized from d-galactose and d-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (−)- daucic acid to have d-lyxo-configuration 46 rather than the previously assigned d-xylo ...

Related Articles:

(−)??Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications

[Lichtenthaler, Frieder W.; Nakamura, Katsumi; Klotz, Juergen Angewandte Chemie - International Edition, 2003 , vol. 42, # 47 p. 5838 - 5843]

Syntheses of derivatives of lacto-N-biose. I. 4, 6-Di-O-acetyl-3-O-(tetra-O-acetyl-β-d-galactopyranosyl)-2-deoxy-2-phthalimido-α, β-d-glucopyranosyl chloride

[Lemieux, R. U.; Abbas, S. Z.; Chung, B. Y. Canadian Journal of Chemistry, 1982 , vol. 60, p. 58 - 62]

Syntheses of derivatives of lacto-N-biose. I. 4, 6-Di-O-acetyl-3-O-(tetra-O-acetyl-β-d-galactopyranosyl)-2-deoxy-2-phthalimido-α, β-d-glucopyranosyl chloride

[Lemieux, R. U.; Abbas, S. Z.; Chung, B. Y. Canadian Journal of Chemistry, 1982 , vol. 60, p. 58 - 62]

Preparation of 1, 2-cis-glycosyl cyanides by the stereoselective reduction of acetylated l-bromo-d-glycosyl cyanioes

[Somsak, Laszlo; Batta, Gyula; Farkas, Istvan Tetrahedron Letters, 1986 , vol. 27, # 48 p. 5877 - 5880]

Preparation of 2, 6??anhydro??3??deoxyhept??(or hex??) 2??enononitriles (1??cyanoglycals) from 1??bromo??D??glycosyl cyanides with zinc under aprotic conditions

[Somsak, Laszlo; Bajza, Istvan; Batta, Gyula Liebigs Annalen der Chemie, 1990 , # 12 p. 1265 - 1268]

More Articles...