TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycoside for anomeric protection

Minoru Izumi; Koichi Fukase; Shoichi Kusumoto

doi:10.1271/bbb.66.211

TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycoside for anomeric protection

Minoru Izumi, Koichi Fukase, Shoichi Kusumoto

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

26 Citations (Scopus)

Abstract

Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co₂(CO)₈ and TFA in CH₂Cl₂via the formation of an alkyne–Co complex.

Original language	English
Pages (from-to)	211-214
Number of pages	4
Journal	Bioscience, Biotechnology and Biochemistry
Volume	66
Issue number	1
DOIs	https://doi.org/10.1271/bbb.66.211
Publication status	Published - 2002
Externally published	Yes

Keywords

Acid catalyst
Fischer glycosidation
Protective group
TMSCl

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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10.1271/bbb.66.211

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title = "TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycoside for anomeric protection",

abstract = "Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2via the formation of an alkyne–Co complex.",

keywords = "Acid catalyst, Fischer glycosidation, Protective group, TMSCl",

author = "Minoru Izumi and Koichi Fukase and Shoichi Kusumoto",

note = "Funding Information: The present work was ˆnancially supported in part by ``Research for the Future'' program No. 97L00502 from the Japan Society for the Promotion of Science, by special coordination funds from the Science and Technology Agency of the Japanese Government, and by grant-aid for scientiˆc research Nos. 09044086 and 12640571 from the Ministry of Education, Science and Culture, Japan.",

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doi = "10.1271/bbb.66.211",

language = "English",

volume = "66",

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TY - JOUR

T1 - TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycoside for anomeric protection

AU - Izumi, Minoru

AU - Fukase, Koichi

AU - Kusumoto, Shoichi

N1 - Funding Information: The present work was ˆnancially supported in part by ``Research for the Future'' program No. 97L00502 from the Japan Society for the Promotion of Science, by special coordination funds from the Science and Technology Agency of the Japanese Government, and by grant-aid for scientiˆc research Nos. 09044086 and 12640571 from the Ministry of Education, Science and Culture, Japan.

PY - 2002

Y1 - 2002

N2 - Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2via the formation of an alkyne–Co complex.

AB - Practical Fischer glycosidation was effected at room temperature or 60°C by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co2(CO)8 and TFA in CH2Cl2via the formation of an alkyne–Co complex.

KW - Acid catalyst

KW - Fischer glycosidation

KW - Protective group

KW - TMSCl

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SN - 0916-8451

VL - 66

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JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 1

ER -

TMSCl as a mild and effective source of acidic catalysis in fischer glycosidation and use of propargyl glycoside for anomeric protection

Abstract

Keywords

ASJC Scopus subject areas

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