Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls

G. J.P.H. Boons; C. J.J. Elie; G. A. van der Matel; J. H. van Boom

doi:10.1016/0040-4039(90)80107-W

Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls

G. J.P.H. Boons^*
, C. J.J. Elie
, G. A. van der Matel
, J. H. van Boom

^*Corresponding author for this work

Leiden University
extern

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

Abstract

The reagent (phenyldimethylsilyl)methoxymethyl chioride (SMOM-Cl) proved to be very convenient for the formation of the corresponding SMOM ethers of primary and secondary hydroxyls of sugars. Further, (phenyldimethylsilyl)methanol (SMOH), the precursor of SMOM-Cl, could be used for the protection of the anomeric centre with the SM group. Both protecting groups can be removed smoothly by oxidation with KBr/AcOOH, and are compatible with protecting group manipulations in sugar chemistry.

Original language	English
Pages (from-to)	2197-2200
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	15
DOIs	https://doi.org/10.1016/0040-4039(90)80107-W
Publication status	Published - 1 Jan 1990
Externally published	Yes

Funding

This work was supported by the WHO Program for Vaccine Development.

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title = "Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls",

abstract = "The reagent (phenyldimethylsilyl)methoxymethyl chioride (SMOM-Cl) proved to be very convenient for the formation of the corresponding SMOM ethers of primary and secondary hydroxyls of sugars. Further, (phenyldimethylsilyl)methanol (SMOH), the precursor of SMOM-Cl, could be used for the protection of the anomeric centre with the SM group. Both protecting groups can be removed smoothly by oxidation with KBr/AcOOH, and are compatible with protecting group manipulations in sugar chemistry.",

author = "Boons, \{G. J.P.H.\} and Elie, \{C. J.J.\} and \{van der Matel\}, \{G. A.\} and \{van Boom\}, \{J. H.\}",

year = "1990",

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doi = "10.1016/0040-4039(90)80107-W",

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T1 - Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls

AU - Boons, G. J.P.H.

AU - Elie, C. J.J.

AU - van der Matel, G. A.

AU - van Boom, J. H.

PY - 1990/1/1

Y1 - 1990/1/1

N2 - The reagent (phenyldimethylsilyl)methoxymethyl chioride (SMOM-Cl) proved to be very convenient for the formation of the corresponding SMOM ethers of primary and secondary hydroxyls of sugars. Further, (phenyldimethylsilyl)methanol (SMOH), the precursor of SMOM-Cl, could be used for the protection of the anomeric centre with the SM group. Both protecting groups can be removed smoothly by oxidation with KBr/AcOOH, and are compatible with protecting group manipulations in sugar chemistry.

AB - The reagent (phenyldimethylsilyl)methoxymethyl chioride (SMOM-Cl) proved to be very convenient for the formation of the corresponding SMOM ethers of primary and secondary hydroxyls of sugars. Further, (phenyldimethylsilyl)methanol (SMOH), the precursor of SMOM-Cl, could be used for the protection of the anomeric centre with the SM group. Both protecting groups can be removed smoothly by oxidation with KBr/AcOOH, and are compatible with protecting group manipulations in sugar chemistry.

UR - https://www.scopus.com/pages/publications/0025219972

U2 - 10.1016/0040-4039(90)80107-W

DO - 10.1016/0040-4039(90)80107-W

M3 - Article

AN - SCOPUS:0025219972

SN - 0040-4039

VL - 31

SP - 2197

EP - 2200

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls

Abstract

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