New procedure for the preparation of 2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside and other alkyl β-glycosides

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 609-610

  Sowell, C Gregory ^a   Livesay, Mark T ^a   Johnson, David A ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030032060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02233-3     Document Type: Article

References (16)

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5. (a) Ogawa, Y.; Fujishima, Y.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1990, 197, 281-288.
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10. For a recent review on the glycosylation of 2-amino-2-deoxy carbohydrates including 1-O-acetylated derivatives, see: Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167-1195.
11. Koto, S.; Morishima, N.; Takenaka, K.; Kanemitsu, K.; Shimoura, N.; Kase, M.; Kojiro, S.; Nakamura, T.; Kawase, T.; Zen, S. Bull. Chem. Soc. Jpn. 1989, 62, 3549-3566.
12. 12 However, in the case of weakly nucleophilic trichloroethanol, virtually none of the β-glycoside 1g is formed in the absence of the azeotrope.
13. Helferich, B.; Schmitz-Hillebrecht, E. Chem. Ber. 1933, 660, 378-383.
14. Hurd, C.D.; Bonner, W.A. J. Org. Chem. 1946, 11, 50-54.
15. 1H-NMR spectra of the products.
16. Srivastava, V.K. Carbohydr. Res. 1982, 103, 286-292.