1,2- trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis

Milandip Karak, Yohei Joh, Masahiko Suenaga, Tohru Oishi, Kohei Torikai

研究成果: ジャーナルへの寄稿記事

抄録

The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.

元の言語英語
ジャーナルOrganic Letters
DOI
出版物ステータス出版済み - 1 1 2019

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Glycosylation
Stereoselectivity
Oligosaccharides
linkages
reactivity
assembly
selectivity
Ions
synthesis
ions

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

これを引用

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title = "1,2- trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis",
abstract = "The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.",
author = "Milandip Karak and Yohei Joh and Masahiko Suenaga and Tohru Oishi and Kohei Torikai",
year = "2019",
month = "1",
day = "1",
doi = "10.1021/acs.orglett.9b00220",
language = "English",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",

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TY - JOUR

T1 - 1,2- trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups

T2 - Application to One-Pot Oligosaccharide Synthesis

AU - Karak, Milandip

AU - Joh, Yohei

AU - Suenaga, Masahiko

AU - Oishi, Tohru

AU - Torikai, Kohei

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.

AB - The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.

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U2 - 10.1021/acs.orglett.9b00220

DO - 10.1021/acs.orglett.9b00220

M3 - Article

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -