On the basis for regioselective oxidation within a tetragalloylpyranose substrate

Ken S. Feldman; Kendra L. Hunter

doi:10.1016/S0040-4039(98)01986-8

On the basis for regioselective oxidation within a tetragalloylpyranose substrate

Ken S. Feldman
, Kendra L. Hunter

Chemistry

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

3 Scopus citations

Abstract

Lead (IV)-mediated oxidation of a benzyl 2,3,4,6- tetragalloylglucopyranoside leads only to coupling at the O(4)/O(6) galloyls. Competitive oxidation experiments with a series of positionally distinct phenolic galloyl analogs furnishes evidence that this unexpected regioselectivity stems from preferential oxidation at the O(6) galloyl ring. Companion studies with electronically dissimilar analogs provide support for a through-space component to O(6) galloyl oxidation selectivity in addition to steric and inductive influences.

Original language	English (US)
Pages (from-to)	8943-8946
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(98)01986-8
State	Published - Dec 3 1998

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)01986-8

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title = "On the basis for regioselective oxidation within a tetragalloylpyranose substrate",

abstract = "Lead (IV)-mediated oxidation of a benzyl 2,3,4,6- tetragalloylglucopyranoside leads only to coupling at the O(4)/O(6) galloyls. Competitive oxidation experiments with a series of positionally distinct phenolic galloyl analogs furnishes evidence that this unexpected regioselectivity stems from preferential oxidation at the O(6) galloyl ring. Companion studies with electronically dissimilar analogs provide support for a through-space component to O(6) galloyl oxidation selectivity in addition to steric and inductive influences.",

author = "Feldman, \{Ken S.\} and Hunter, \{Kendra L.\}",

note = "Funding Information: We thank the NIH (GM35727) for financial support of this work.",

year = "1998",

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doi = "10.1016/S0040-4039(98)01986-8",

language = "English (US)",

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journal = "Tetrahedron Letters",

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T1 - On the basis for regioselective oxidation within a tetragalloylpyranose substrate

AU - Feldman, Ken S.

AU - Hunter, Kendra L.

N1 - Funding Information: We thank the NIH (GM35727) for financial support of this work.

PY - 1998/12/3

Y1 - 1998/12/3

N2 - Lead (IV)-mediated oxidation of a benzyl 2,3,4,6- tetragalloylglucopyranoside leads only to coupling at the O(4)/O(6) galloyls. Competitive oxidation experiments with a series of positionally distinct phenolic galloyl analogs furnishes evidence that this unexpected regioselectivity stems from preferential oxidation at the O(6) galloyl ring. Companion studies with electronically dissimilar analogs provide support for a through-space component to O(6) galloyl oxidation selectivity in addition to steric and inductive influences.

AB - Lead (IV)-mediated oxidation of a benzyl 2,3,4,6- tetragalloylglucopyranoside leads only to coupling at the O(4)/O(6) galloyls. Competitive oxidation experiments with a series of positionally distinct phenolic galloyl analogs furnishes evidence that this unexpected regioselectivity stems from preferential oxidation at the O(6) galloyl ring. Companion studies with electronically dissimilar analogs provide support for a through-space component to O(6) galloyl oxidation selectivity in addition to steric and inductive influences.

UR - https://www.scopus.com/pages/publications/0032480927

UR - https://www.scopus.com/pages/publications/0032480927#tab=citedBy

U2 - 10.1016/S0040-4039(98)01986-8

DO - 10.1016/S0040-4039(98)01986-8

M3 - Article

AN - SCOPUS:0032480927

SN - 0040-4039

VL - 39

SP - 8943

EP - 8946

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

On the basis for regioselective oxidation within a tetragalloylpyranose substrate

Abstract

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