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Original Articles

Diastereoselective Preparation of a New Class of Deoxy λ5 Phospha Sugar Derivatives

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Pages 483-492 | Published online: 09 Aug 2006

References and Notes

  • Gallagher , M. J. and Ranasinghe , M. G. 1996 . Stereoselective route to a new class of phosphasugars. Novel analogues of 2‐deoxyglucose and 2‐deoxyallose . J. Org. Chem., , 61 ( 2 ) : 436 – 437 .
  • Yamamoto , H. and Inokawa , S. 1984 . Sugar analogs having phosphorus in the hemiacetal ring . Adv. Carbohydr. Chem. Biochem. , 42 : 135 – 391 .
  • Yamamoto , H. , Hanaya , T. , Kawamoto , H. and Inokawa , S. 1988 . Synthesis and structural analysis of 5‐deoxy‐5‐[(R,S)‐ethylphosphinyl]‐α,β‐L‐idopyranoses . J. Org. Chem. , 53 ( 20 ) : 4790 – 4793 .
  • Inouye , S. , Tsuruoka , T. and Niida , T. 1966 . Structure of nojirimycin, sugar antibiotic with nitrogen in the ring . J. Antibiot. Ser. A. , 19 ( 6 ) : 288 – 292 .
  • Inouye , S. , Tsuruoka , T. , Ito , T. and Niida , T. 1968 . Structure and synthesis of nojirimycin . Tetrahedron , 24 ( 5 ) : 2125 – 2144 .
  • Nayak , U. G. and Whistler , R. L. 1969 . Synthesis of 5‐thio‐D‐glucose . J. Org. Chem. , 34 ( 1 ) : 97 – 100 .
  • Yamashita , M. , Yamada , M. , Sugiura , M. , Nomoto , H. and Oshikawa , T. 1987 . Functional group interconversion of a β‐nitro group of phosphorus compounds and synthesis of some phosphino sugars . Nippon Kagaku Kaishi , : 1207 – 1213 .
  • Takayanagi , H. , Yamashita , M. , Seo , K. , Yoshida , H. , Ogata , T. and Inokawa , S. 1974 . Synthesis of 6‐nitro‐D‐glucopyranose having phosphorus in the hemiacetal ring . Carbohydr. Res. , 38 : C19 – C21 .
  • Yamamoto , H. , Hosoyamada , C. , Kawamoto , H. , Inokawa , S. , Yamashita , M. , Armour , M. A. and Nakashima , T. T. 1982 . Synthesis of 1,2,4‐tri‐O‐acetyl‐3,6‐di‐O‐benzyl‐5‐deoxy‐5‐C‐[(S)‐phenylphosphinyl]‐β‐D‐glucopyranose: the first gluco type of hexopyranose derivative having phosphorus in the hemiacetal ring . Carbohydr. Res. , 102 : 159 – 167 .
  • Yamamoto , H. , Hanaya , T. , Kawamoto , H. , Inokawa , S. , Yamashita , M. and Nakashima , T. T. 1985 . Synthesis and structural analysis of 5‐deoxy‐5‐C‐(hydroxyphosphinyl)‐D‐xylo‐and‐glucopyranoses . J. Org. Chem. , 50 ( 19 ) : 3516 – 3521 .
  • Quin , L. D. , Gratz , J. P. and Barket , T. P. 1968 . Structure of diene‐phosphonous dihalide addition products and of derived phospholenes and phospholene oxides . J. Org. Chem. , 33 ( 3 ) : 1034 – 1041 .
  • Quin , L. D. 1981 . The heterocyclic chemistry of phosphorus 350 New York : Wiley‐Interscience .
  • Hanaya , T. and Yamamoto , H. 1989 . Synthesis and structural analysis of 4‐deoxy‐4‐(hydroxyphosphinyl and phenylphosphinyl)‐D‐ribofuranoses . Bull. Chem. Soc. Jpn. , 62 : 2320 – 2327 .
  • Crystal data of 6a: C12H14O5PBr, M = 349.12, colorless, prismatic, 0.30 × 0.30 × 0.20 mm, orthorhombic, Pna2 1 (no. 33), a = 7.016(4) Å, b = 18.560(5) Å, c = 11.003(4) Å, T = 296 K, Observations [I > 3.00σ(I)] = 847, Variables = 193, Reflection/Parameter ratio = 4.39, R, Rw = 0.067, 0.049. Full crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Center. Copies may be requested free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)‐1223‐336033, or e-mail: [email protected]]
  • Cha , J. K. , Christ , W. J. and Kishi , Y. 1984 . On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule . Tetrahedron , 40 ( 12 ) : 2247 – 2255 .

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