Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions

Authors
Adinolfi, M Barone, G Guariniello, L Iadonisi, A
Citation
M. Adinolfi et al., Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions, TETRAHEDR L, 40(48), 1999, pp. 8439-8441
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
48
Year of publication
1999
Pages
8439 - 8441
Database
ISI
SICI code
0040-4039(19991126)40:48<8439:FCOCBE>2.0.ZU;2-O
Abstract
Benzyl ether and benzylidene acetal carbohydrate protecting groups can be s electively cleaved by reaction with sodium bromate/sodium dithionite in eth yl acetate/water. Under the mild (room temperature, short reaction time) co nditions needed, a variety of other protecting functionalities such as acet yl, chloroacetyl, benzoyl, pivaloyl, tosyl, t-butyldimethylsilyl, trityl, a nd isopropylidene groups remain unaffected. (C) 1999 Elsevier Science Ltd. All rights reserved.