Peculiar side-chain fission of steroidal glycosides

Tetrahedron Letters

Volumn 44, Issue 17, 2003, Pages 3509-3511

  Nafady, Alaa Mohamed ^a   El Shanawany, Mohamed Ahmed ^b   Mohamed, Mahmoud Hamed ^c   Hassanean, Hashim Abdel Halim ^b   Zhu, Xing Hua ^a   Yoshihara, Tsutomu ^a   Okawa, Masafumi ^a   Ikeda, Tsuyoshi ^a   Nohara, Toshihiro ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b Assiut University   (Egypt)

^c Al Azhar University   (Egypt)

Author keywords

16,22 dicarbonyl cholestanol; 23,26 oxygenated spirostanol; Side chain fission; Steroidal glycoside

Indexed keywords

GLYCOSIDE; LACTONE DERIVATIVE; STEROID;

ALKALINITY; ARTICLE; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROLYSIS; OXYGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0037459888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00689-0     Document Type: Article

References (14)

1. Honbu T., Ikeda T., Zhu X.-H., Yoshihara O., Okawa M., Nafady A.M., Nohara T. J. Nat. Prod. 65:2002;1918-1920.
2. 5): δ 37.5, 30.2, 78.1, 39.0, 140.8, 121.8, 32.3, 31.7, 50.4, 37.2, 21.1, 40.0, 41.1, 56.7, 32.5 (C-1-15), 81.17/81.23 (C-16), 64.0/64.4 (C-17), 16.4/16.6 (C-18), 19.3 (C-19), 38.1 (C-20), 16.25/16.30 (C-21), 109.2/109.9 (C-22), 81.5/84.1 (C-23), 32.6/34.8 (C-24), 38.2 (C-25), 99.2/105.6 (C-26), 13.4/17.3 (C-27), 100.3, 78.7, 77.0, 77.8, 78.0, 61.3 (glc C-1-6), 102.0, 72.6, 72.8, 74.2, 69.5, 18.5 [-glc-(2-1)- rha C-1-6 ], 102.9, 72.6, 72.8, 73.9, 70.4, 18.7 [-glc-(4-1)- rha C-1-6 ]. See: Zhu, X.-H.; Tsumagari, H.; Honbu, T.; Ikeda, T.; Ono, M.; Nohara, T. Symposium Papers of the 43rd Symposium on the Chemistry of Natural Products, Tokyo, 2001, pp. 335-340.
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7. The analogous glycoside carrying the sugar A with 2 also gave 4 in 61% yield by the same reaction.
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14. 5): the signals due to the sapogenol part were superimposable on those of 5 ; sugar moiety, δ 100.0, 77.8, 88.2, 77.4, 74.7, 62.4 (inner glc C-1-6), 102.4, 72.5, 72.8, 74.1, 69.6, 18.7 (terminal rha C-1-6), 105.5, 74.7, 77.9, 70.7, 67.3 (terminal xyl C-1-5).