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Volumn 55, Issue 34, 1999, Pages 10315-10324

Efficient stereoselective synthesis of α-C-glycopyranosides using 2,2'- azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70]

Author keywords

Glycosidation; Glycosides; Radical reactions; Stereocontrol

Indexed keywords

GLYCOPYRANOSIDE; METHYL GROUP; NATURAL PRODUCT; VALERONITRILE;

EID: 0033588359     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00587-6     Document Type: Article
Times cited : (12)

References (40)
  • 22
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    • U.S. Patent 2,586,995 (1952)
    • (a) Robertson, J. A. U. S. Patent 2,586,995 (1952) [Chem. Abstr. 1952, 46, 9579c].
    • (1952) Chem. Abstr. , vol.46
    • Robertson, J.A.1
  • 24
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    • Jpn. Kokai Tokkyo Koho JP 04,66,588 [92,66,588] (Cl. C07F7/12), 02 Mar 1992, Appl. 90/172,449,29 Jun 1990; 4pp.
    • (c) Shinohara, N.; Kudo, M.; Iwabuchi, M. Jpn. Kokai Tokkyo Koho JP 04,66,588 [92,66,588] (Cl. C07F7/12), 02 Mar 1992, Appl. 90/172,449,29 Jun 1990; 4pp. [Chem. Abstr. 1992, 117, 26799b]
    • (1992) Chem. Abstr. , vol.117
    • Shinohara, N.1    Kudo, M.2    Iwabuchi, M.3
  • 25
    • 4243380706 scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 06,172,232 [94,172,232] (Cl. C07C22/04), 21 Jun 1994, Appl. 92/329,416,09 Dec 1992; 6pp.
    • (d) Satsuka, H.; Takasu, Y. Jpn. Kokai Tokkyo Koho JP 06,172,232 [94,172,232] (Cl. C07C22/04), 21 Jun 1994, Appl. 92/329,416,09 Dec 1992; 6pp. [Chem. Abstr. 1994, 121, 230457a]
    • (1994) Chem. Abstr. , vol.121
    • Satsuka, H.1    Takasu, Y.2
  • 26
    • 4243342062 scopus 로고    scopus 로고
    • Eur. Pat. Appl. EP 709,369 (Cl. C07C253/30),1 May 1996, JP Appl. 94/289,079, 27 Oct 1994; 7pp. 2,2′-Azobis(2,4-dimethyl-4-methoxy- valeronitrile) is commercially available from Wako Pure Chemical Ind., Ltd., (Japan), and V-70 is its trade name. This compound should be stored below -10 °C to prevent any decomposition. V-70 is stable in a refrigerator for a few months, and the pure V-70 can be easily obtained by the following procedure: V-70 (10.0 g, ca. 90% content) was added to dry acetone (20 ml) at -10 °C with stirring. The heterogeneous solution was stirred for 30 min at -10 °C. Collecting the crystalline precipitates afforded 6.2g of pure V-70 (62%, >99% content)
    • (e) Katsura, T.; Shiratani, H. Eur. Pat. Appl. EP 709,369 (Cl. C07C253/30),1 May 1996, JP Appl. 94/289,079, 27 Oct 1994; 7pp. [Chem. Abstr. 1996, 125, 58121f]. 2,2′-Azobis(2,4-dimethyl-4-methoxy- valeronitrile) is commercially available from Wako Pure Chemical Ind., Ltd., (Japan), and V-70 is its trade name. This compound should be stored below -10 °C to prevent any decomposition. V-70 is stable in a refrigerator for a few months, and the pure V-70 can be easily obtained by the following procedure: V-70 (10.0 g, ca. 90% content) was added to dry acetone (20 ml) at -10 °C with stirring. The heterogeneous solution was stirred for 30 min at -10 °C. Collecting the crystalline precipitates afforded 6.2g of pure V-70 (62%, >99% content).
    • (1996) Chem. Abstr. , vol.125
    • Katsura, T.1    Shiratani, H.2
  • 31
    • 0009577323 scopus 로고    scopus 로고
    • note
    • V-70L: low melting point diastereomer, mp. 58 °C.; V-70H: high melting point diastereomer, mp. 107 °C.
  • 32
    • 0009577443 scopus 로고    scopus 로고
    • note
    • The stereochemistry of all new compounds were assigned on the basis of the coupling constant (J) of the anomeric proton and the adjacent axial proton of gulycopyranoside ring. (formula presented)


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