Reductive deprotection of propargyl ether by a SmI2-amine-water system and its application to polymer-supported oligosaccharide synthesis

Shino Manabe; Akiharu Ueki; Yukishige Ito

doi:10.1016/j.tetlet.2008.06.081

Reductive deprotection of propargyl ether by a SmI₂-amine-water system and its application to polymer-supported oligosaccharide synthesis

Shino Manabe, Akiharu Ueki, Yukishige Ito

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

12 Citations (Scopus)

Abstract

A SmI₂-amine-water system instantaneously deprotected aryl and alkyl propargyl ethers in a reductive manner. The utility of the propargyl group as a protecting group in oligosaccharide synthesis, and its application to polymer-supported oligosaccharide synthesis is described.

Original language	English
Pages (from-to)	5159-5161
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2008.06.081
Publication status	Published - 2008 Aug 25
Externally published	Yes

Keywords

Deprotection reaction
Oligosaccharide synthesis
Propargyl ether
Protecting group
SmI

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2008.06.081

Cite this

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title = "Reductive deprotection of propargyl ether by a SmI2-amine-water system and its application to polymer-supported oligosaccharide synthesis",

abstract = "A SmI2-amine-water system instantaneously deprotected aryl and alkyl propargyl ethers in a reductive manner. The utility of the propargyl group as a protecting group in oligosaccharide synthesis, and its application to polymer-supported oligosaccharide synthesis is described.",

keywords = "Deprotection reaction, Oligosaccharide synthesis, Propargyl ether, Protecting group, SmI",

author = "Shino Manabe and Akiharu Ueki and Yukishige Ito",

note = "Funding Information: We thank Ms. A. Takahashi for her technical assistance. S.M. thanks the JSPS for a Grant-in Aid for Scientific Research (C) (Grant No. 19590032). ",

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journal = "Tetrahedron Letters",

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T1 - Reductive deprotection of propargyl ether by a SmI2-amine-water system and its application to polymer-supported oligosaccharide synthesis

AU - Manabe, Shino

AU - Ueki, Akiharu

AU - Ito, Yukishige

N1 - Funding Information: We thank Ms. A. Takahashi for her technical assistance. S.M. thanks the JSPS for a Grant-in Aid for Scientific Research (C) (Grant No. 19590032).

PY - 2008/8/25

Y1 - 2008/8/25

N2 - A SmI2-amine-water system instantaneously deprotected aryl and alkyl propargyl ethers in a reductive manner. The utility of the propargyl group as a protecting group in oligosaccharide synthesis, and its application to polymer-supported oligosaccharide synthesis is described.

AB - A SmI2-amine-water system instantaneously deprotected aryl and alkyl propargyl ethers in a reductive manner. The utility of the propargyl group as a protecting group in oligosaccharide synthesis, and its application to polymer-supported oligosaccharide synthesis is described.

KW - Deprotection reaction

KW - Oligosaccharide synthesis

KW - Propargyl ether

KW - Protecting group

KW - SmI

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DO - 10.1016/j.tetlet.2008.06.081

M3 - Article

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SN - 0040-4039

VL - 49

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EP - 5161

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -