Allyl C-glycosidations of totally unprotected glycals and allyltrimethylsilane with trimethylsilyl trifluoromethanesulfonate (TMSOTf)

Kazunobu Toshima; Toru Ishizuka; Goh Matsuo; Masaya Nakata

doi:10.1016/S0040-4039(00)77276-5

Allyl C-glycosidations of totally unprotected glycals and allyltrimethylsilane with trimethylsilyl trifluoromethanesulfonate (TMSOTf)

Kazunobu Toshima, Toru Ishizuka, Goh Matsuo, Masaya Nakata

Department of Applied Chemistry

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

30 Citations (Scopus)

Abstract

Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.

Original language	English
Pages (from-to)	5673-5676
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(00)77276-5
Publication status	Published - 1994 Aug 1

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.",

author = "Kazunobu Toshima and Toru Ishizuka and Goh Matsuo and Masaya Nakata",

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AU - Toshima, Kazunobu

AU - Ishizuka, Toru

AU - Matsuo, Goh

AU - Nakata, Masaya

PY - 1994/8/1

Y1 - 1994/8/1

N2 - Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.

AB - Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10∼13 to furnish the unprotected and 2,3-unsaturated allyl α-C-glycosides 6∼9 in high yields, respectively.

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Allyl C-glycosidations of totally unprotected glycals and allyltrimethylsilane with trimethylsilyl trifluoromethanesulfonate (TMSOTf)

Abstract

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