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Short Note

Benzyl-3-deoxy-3(phenethylamino) b-L-Xylopyranoside

by
Fulgentius N. Lugemwa
* and
Laura Denison
Department of Chemistry, Murray State University, P.O. Box 9, Murray, KY 42071-0009, USA
*
Author to whom correspondence should be addressed.
Molecules 1998, 3(4), M76; https://doi.org/10.3390/M76
Submission received: 7 April 1998 / Published: 15 April 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 03 m76 i001
A mixture of benzyl 2,3-anhydro-b-L-ribopyranoside (1) [1] (0.88 g, 4 mmol) and phenethylamine (5 mL) was gently refluxed. After 15 minutes the mixture was cooled, and 10% aqueous ethanol (15 mL) added to precipitate the product. The resulting solid was filtered and recrystallized from 98% ethanol to provide benzyl-3-deoxy-3(phenethylamino)-b-L-xylopyranoside,(2), (1.2 g, 87%).
M.p. 179-181deg.C.
[a]D +44o (c 0.01, 1M HCl).
1H NMR (200 MHz, Me2SO-d6) d 1.85 (bs, 1H, NH), 2.35 (t, J = 9.16, 8.00 Hz, 1H, H-3), 2.74 (m, 2H), 2.95-3.20 (m, 3H), 3.35 (m, 2H), 3.75 (dd, J = 4.52, 10.78 Hz, 1H, H-5e), 4.25 (d, J = 7.32 Hz, 1H, H-1), 4.54 (d, J = 12.37 Hz, 1H, -OCH2Ar), 4.77 (d, J = 12.37 Hz, 1H, -OCH2Ar), 4.90 (d, J = 5.66 Hz, 1H, -OH), 5.15 (d, J = 5.25 Hz, 1H, -OH).
13C NMR (50.1 MHz, Me2SO-d6) d 38.82, 50.30, 65.15, 66.89, 69.40, 69.79, 72.28, 103.33 (C-1), 126.02, 127.64, 127.82, 128.41, 128.48, 128.84, 139.10, 140.77. Four signals for aromatic carbons overlapped.
Acknowledgement: The authors gratefully acknowledge financial support from the Research Corporation-Cottrell College Science Award.

References and Notes

  1. Lugemwa, F. N.; Denison, L. J. Carbohydr. Chem. 1997, 16, 1433–1443. [CrossRef]
Sample availability: 0.5 g.

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MDPI and ACS Style

Lugemwa, F.N.; Denison, L. Benzyl-3-deoxy-3(phenethylamino) b-L-Xylopyranoside. Molecules 1998, 3, M76. https://doi.org/10.3390/M76

AMA Style

Lugemwa FN, Denison L. Benzyl-3-deoxy-3(phenethylamino) b-L-Xylopyranoside. Molecules. 1998; 3(4):M76. https://doi.org/10.3390/M76

Chicago/Turabian Style

Lugemwa, Fulgentius N., and Laura Denison. 1998. "Benzyl-3-deoxy-3(phenethylamino) b-L-Xylopyranoside" Molecules 3, no. 4: M76. https://doi.org/10.3390/M76

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