The anomeric Pudovik rearrangement

Spencer Knapp; Kehinde Ajayi

doi:10.1016/j.tetlet.2007.01.081

The anomeric Pudovik rearrangement

Spencer Knapp, Kehinde Ajayi

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

6 Scopus citations

Abstract

The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.

Original language	English (US)
Pages (from-to)	1945-1949
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2007.01.081
State	Published - Mar 12 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.01.081

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title = "The anomeric Pudovik rearrangement",

abstract = "The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.",

author = "Spencer Knapp and Kehinde Ajayi",

note = "Funding Information: We are grateful to NIH (AI055760) for financial support. K.A. thanks the GAANN program for a graduate fellowship. ",

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doi = "10.1016/j.tetlet.2007.01.081",

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T1 - The anomeric Pudovik rearrangement

AU - Knapp, Spencer

AU - Ajayi, Kehinde

N1 - Funding Information: We are grateful to NIH (AI055760) for financial support. K.A. thanks the GAANN program for a graduate fellowship.

PY - 2007/3/12

Y1 - 2007/3/12

N2 - The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.

AB - The O,O-dibenzyl-S-glycosyl phosphothioite derived from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-glucopyranose rearranges under the influence of triethylborane and air to provide the corresponding 1-C-pyranosyl-O,O-dibenzylphosphonothioate, a new type of carbohydrate derivative. The isomeric beta phosphothioite is compared, and evidence of a radical chain mechanism for the Pudovik rearrangement is presented.

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DO - 10.1016/j.tetlet.2007.01.081

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SP - 1945

EP - 1949

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

The anomeric Pudovik rearrangement

Abstract

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