Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates

Kaname Sasaki; Takayuki Wakamatsu; Shuichi Matsumura; Kazunobu Toshima

doi:10.1016/j.tetlet.2006.09.091

Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates

Kaname Sasaki, Takayuki Wakamatsu, Shuichi Matsumura, Kazunobu Toshima

Department of Applied Chemistry

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

9 Citations (Scopus)

Abstract

A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al₂O₃ in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.

Original language	English
Pages (from-to)	8271-8274
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2006.09.091
Publication status	Published - 2006 Nov 20

Keywords

Carbohydrates
Chemoselectivity
Hydrogenation
Hydrogenolysis
Tetrahydropyrans

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.09.091

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title = "Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates",

abstract = "A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al2O3 in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.",

keywords = "Carbohydrates, Chemoselectivity, Hydrogenation, Hydrogenolysis, Tetrahydropyrans",

author = "Kaname Sasaki and Takayuki Wakamatsu and Shuichi Matsumura and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by Grant-in-Aid for the 21st Century COE Program {\textquoteleft}KEIO Life Conjugated Chemistry{\textquoteright}, for Scientific Research on Priority Areas 18032068 and for JSPS Fellows 18 ∗ 6013 from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

year = "2006",

month = nov,

day = "20",

doi = "10.1016/j.tetlet.2006.09.091",

language = "English",

volume = "47",

pages = "8271--8274",

journal = "Tetrahedron Letters",

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number = "47",

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TY - JOUR

T1 - Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates

AU - Sasaki, Kaname

AU - Wakamatsu, Takayuki

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by Grant-in-Aid for the 21st Century COE Program ‘KEIO Life Conjugated Chemistry’, for Scientific Research on Priority Areas 18032068 and for JSPS Fellows 18 ∗ 6013 from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2006/11/20

Y1 - 2006/11/20

N2 - A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al2O3 in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.

AB - A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al2O3 in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.

KW - Carbohydrates

KW - Chemoselectivity

KW - Hydrogenation

KW - Hydrogenolysis

KW - Tetrahydropyrans

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DO - 10.1016/j.tetlet.2006.09.091

M3 - Article

AN - SCOPUS:33750018084

SN - 0040-4039

VL - 47

SP - 8271

EP - 8274

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates

Abstract

Keywords

ASJC Scopus subject areas

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