Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks Full article
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Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215 |
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| Output data | Year: 2011, Volume: 346, Number: 1, Pages: 7-15 Pages count : 9 DOI: 10.1016/j.carres.2010.11.002 | ||
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Abstract:
β-d-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-α-d-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to α-(1→5)-linked disaccharide thioglycosides with 5′-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides.
Cite:
Podvalnyy N.M.
, Sedinkin S.L.
, Abronina P.I.
, Zinin A.I.
, Fedina K.G.
, Torgov V.I.
, Kononov L.O.
Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
Carbohydrate Research. 2011. V.346. N1. P.7-15. DOI: 10.1016/j.carres.2010.11.002 WOS Scopus OpenAlex
Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
Carbohydrate Research. 2011. V.346. N1. P.7-15. DOI: 10.1016/j.carres.2010.11.002 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000286715700001 |
| Scopus: | 2-s2.0-78650205545 |
| OpenAlex: | W1991529548 |