Facile conversion of O-silyl protected sugars into their corresponding formates using POCl 3·DMF complex

Marta M. Andrade; M. Teresa Barros

doi:10.1016/j.tet.2004.07.056

Facile conversion of O-silyl protected sugars into their corresponding formates using POCl ₃·DMF complex

Marta M. Andrade, M. Teresa Barros

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex POCl ₃·DMF was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue.

Original language	English
Pages (from-to)	9235-9243
Number of pages	9
Journal	Tetrahedron
Volume	60
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2004.07.056
Publication status	Published - 4 Oct 2004

Keywords

Carbohydrates
Regio and chemoselective O-formylation
Vilsmeier-Haack (V-H) complex

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abstract = "The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex POCl 3·DMF was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue.",

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AU - Andrade, Marta M.

AU - Barros, M. Teresa

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N2 - The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex POCl 3·DMF was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue.

AB - The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex POCl 3·DMF was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue.

KW - Carbohydrates

KW - Regio and chemoselective O-formylation

KW - Vilsmeier-Haack (V-H) complex

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DO - 10.1016/j.tet.2004.07.056

M3 - Article

SN - 0040-4020

VL - 60

SP - 9235

EP - 9243

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

Facile conversion of O-silyl protected sugars into their corresponding formates using POCl ₃·DMF complex

Abstract

Keywords

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