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Volumn 61, Issue 16, 1996, Pages 5202-5203

Desymmetrization of a silyl-2,5-cyclohexadiene. Synthesis of (+)-conduritol e and (-)-2-deoxy-allo-inositol

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYINOSITOL; CONDURITOL E; CYCLOHEXANE DERIVATIVE; POLYOL; UNCLASSIFIED DRUG;

EID: 0029743127     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960814r     Document Type: Article
Times cited : (47)

References (47)
  • 9
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    • For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
    • (1994) J. Org. Chem. , vol.59 , pp. 54
    • Takano, S.1    Yoshimitsu, T.2    Ogasawara, K.3
  • 10
    • 37049088912 scopus 로고
    • For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 2907
    • Hudlicky, T.1    Luna, H.2    Olivo, H.F.3    Andersen, C.4    Nugent, T.5    Price, J.D.6
  • 11
    • 0001517733 scopus 로고
    • For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 2335
    • McCasland, G.E.1    Furuta, S.2    Johnson, L.F.3    Shoolery, J.N.4
  • 12
    • 0013555886 scopus 로고
    • For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
    • (1982) Carbohydr. Res. , vol.101 , pp. 209
    • Angyal, S.J.1    Odier, L.2
  • 13
    • 0002780895 scopus 로고
    • For previous asymmetric syntheses of conduritol E: (a) Takano, S.; Yoshimitsu, T.; Ogasawara, K. J. Org. Chem. 1994, 59, 54. (b) Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907. For a previous asymmetric synthesis of 2-deoxy-allo-inositol: (c) McCasland, G. E.; Furuta, S.; Johnson, L. F.; Shoolery, J. N. J. Am. Chem. Soc. 1961, 83, 2335. (d) Angyal, S. J.; Odier, L. Carbohydr. Res. 1982, 101, 209. (e) Angyal, S. J.; Odier, L. Ibid. 1982, 100, 43.
    • (1982) Carbohydr. Res. , vol.100 , pp. 43
    • Angyal, S.J.1    Odier, L.2
  • 35
    • 3643099302 scopus 로고    scopus 로고
    • note
    • Ten to 20% of the corresponding siloxane is sometimes produced during the workup but is easily removed by distillation. The amount of siloxane can be reduced by diluting the reaction mixture prior to aqueous workup.
  • 37
    • 84943847437 scopus 로고
    • 2: Andrianov, K. A.; Delazari, N. V. Dok. Akad. Nauk. SSSR 1958, 122, 393; Chem. Abst. 1959, 53, 2133.
    • (1959) Chem. Abst. , vol.53 , pp. 2133
  • 38
    • 85088232376 scopus 로고    scopus 로고
    • note
    • 4Cl.
  • 39
    • 3643104570 scopus 로고    scopus 로고
    • note
    • The reaction between 3a and AD-mix was complete after 12 h at 0°C and led after careful extraction to the desired 1,2-diol in 65-75% crude yield. The presence of more polar, intractable tetrols in the aqueous phase cannot, however, be excluded.
  • 40
    • 3643074390 scopus 로고    scopus 로고
    • note
    • DMF was used instead of the standard THF-MeOH mixture, which led to incomplete oxidation.
  • 41
    • 85088228769 scopus 로고    scopus 로고
    • note
    • 1H NMR of Mosher's esters.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.