Stereospecific Synthesis of Methyl-6-deoxy-$\beta$-L-idopyranoside

Methyl-6-deoxy-$\beta$-L-idopyranoside의 합성

  • Published : 1986.12.01

Abstract

Methyl-6-deoxy-$\beta$-L-idopyranoside was prepared in good yield by treatment of methyl 2,3,4-tri-O-benzyl-6-deoxy-$\alpha$-D-xylo-hex-5-enopyranoside with H$_2$ on pd, followed by reaction of Na/NH$_3$ at $-50^{\circ}C$. The ratio of L-idopyranoside and D-glucopyranoside was 7 to 1 in 80.7%. It was confirmed that L-idopyranoside was 1C conformation as being expected.

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References

  1. Bull. of the Chem. Society of Japan v.44 Ikeda,D.;Tsuchiya,T.;Y.Umezawas
  2. Carbohydrate Research v.36 Helferich
  3. Chem. Pharm. Bull. v.15 Iwashige,T.;Saeki,H.
  4. Bull. of the Chem. Society of Japan v.49 Koto,S.;Morishima,N.;Miyata,Y.;Zen.S.
  5. Liebigs Ann. Chem. Kuster,M.;Dyong,I.
  6. Can. J. Chem. v.59 Koto,S.;Inada,S.;Yoshida,T.;Toyama,M.;Zen,S.
  7. Syn. Comm. Garegg,O.J.;Samuelsson,B.
  8. Can. J. Chem. v.59 Classon,B.;Garegg,P.J.;Samuelsson,B.
  9. Methods in Carbodydrate Chem. v.8 Horton,D.;Cheung,T.M.;Weckerel,W.
  10. Carbohydrate Research v.115 Ichikawa,Y.;Kuzahara,H.
  11. Carbohydrate Research v.116 Gallagher,T.F.;Horton,D.
  12. Helv. Chim. Acta. v.37 Fisher,R.