A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation

Santosh R. Kotturi; Jason S. Tan; Martin J. Lear

doi:10.1016/j.tetlet.2009.07.020

A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation

Santosh R. Kotturi, Jason S. Tan, Martin J. Lear

SCI - Chemistry

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

11 Citations (Scopus)

Abstract

With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).

Original language	English
Pages (from-to)	5267-5269
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.020
Publication status	Published - 2009 Sep 16

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.07.020

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title = "A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation",

abstract = "With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).",

author = "Kotturi, {Santosh R.} and Tan, {Jason S.} and Lear, {Martin J.}",

note = "Funding Information: Financial support from the NUS Academic Research Fund (AcRF Tier-1: R-143-000-304-112) and a PhD scholarship (to S.R.K.) is greatly appreciated. ",

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T1 - A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation

AU - Kotturi, Santosh R.

AU - Tan, Jason S.

AU - Lear, Martin J.

N1 - Funding Information: Financial support from the NUS Academic Research Fund (AcRF Tier-1: R-143-000-304-112) and a PhD scholarship (to S.R.K.) is greatly appreciated.

PY - 2009/9/16

Y1 - 2009/9/16

N2 - With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).

AB - With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).

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M3 - Article

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VL - 50

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EP - 5269

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation

Abstract

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