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Kornilov AV, Sukhova EV, Nifantiev NE. Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz(2)O or Piv(2)O. Carbohydr Res. 2001;336(4):309-13doi: 10.1016/s0008-6215(01)00272-5.
Kornilov, A. V., Sukhova, E. V., & Nifantiev, N. E. (2001). Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz(2)O or Piv(2)O. Carbohydrate research, 336(4), 309-13. https://doi.org/10.1016/s0008-6215(01)00272-5
Kornilov, A V, et al. "Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz(2)O or Piv(2)O." Carbohydrate research vol. 336,4 (2001): 309-13. doi: https://doi.org/10.1016/s0008-6215(01)00272-5
Kornilov AV, Sukhova EV, Nifantiev NE. Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz(2)O or Piv(2)O. Carbohydr Res. 2001 Dec 07;336(4):309-13. doi: 10.1016/s0008-6215(01)00272-5. PMID: 11728399.
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Carbohydr Res. 2001 Dec 07;336(4):309-13. doi: 10.1016/s0008-6215(01)00272-5.

Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz(2)O or Piv(2)O.

Carbohydrate research

A V Kornilov, E V Sukhova, N E Nifantiev

Affiliations

  1. N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow B-334, Russia.

PMID: 11728399 DOI: 10.1016/s0008-6215(01)00272-5

Abstract

Heating of non-substituted beta-D-glucopyranuronic acids in the presence of pivalic or benzoic anhydride in DMF gives 4-O-monoacylated or 2,4-di-O-acylated 6,3-lactones that can be easily transformed into corresponding methyl uronates bearing free OH-groups at C-2 and C-3 or C-3 only, respectively. This method was used for preparation of selectively 3-O-protected glucuronyl donors of thioglycoside and trichloracetimidate types.

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