Reaction of thiophenol with glucal epoxides: X-ray structure of 3,4,6-tri-O-tert-butyldimethylsilyl-1-S-phenyl-1-thio-α-D-glucopyranoside

Caroline Walford; Richard F W Jackson; Nicholas H Rees; William Clegg; Sarah L Heath

doi:10.1039/a704534d

Reaction of thiophenol with glucal epoxides: X-ray structure of 3,4,6-tri-O-tert-butyldimethylsilyl-1-S-phenyl-1-thio-α-D-glucopyranoside

Caroline Walford, Richard F W Jackson, Nicholas H Rees, William Clegg, Sarah L Heath

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

Abstract

The reaction of the tert-butyldimethylsilyl protected glucal epoxide with thiophenol under a variety of conditions gives three distinct adducts, including the α-phenylthioglycoside, which exists both in soln. and in the solid state in a 1C4 conformation in which the C-2, C-3, C-4 and C-5 substituents are all axial. [on SciFinder(R)]

Original language	English
Pages (from-to)	1855-1856
Number of pages	2
Journal	Chem. Commun. (Cambridge)
Issue number	19
DOIs	https://doi.org/10.1039/a704534d
Publication status	Published - 1997

Keywords

thiophenol reaction glucal epoxide
phenylthioglucopyranoside prepn conformation crystal structure

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title = "Reaction of thiophenol with glucal epoxides: X-ray structure of 3,4,6-tri-O-tert-butyldimethylsilyl-1-S-phenyl-1-thio-α-D-glucopyranoside",

abstract = "The reaction of the tert-butyldimethylsilyl protected glucal epoxide with thiophenol under a variety of conditions gives three distinct adducts, including the α-phenylthioglycoside, which exists both in soln. and in the solid state in a 1C4 conformation in which the C-2, C-3, C-4 and C-5 substituents are all axial. [on SciFinder(R)]",

keywords = "thiophenol reaction glucal epoxide, phenylthioglucopyranoside prepn conformation crystal structure",

author = "Caroline Walford and Jackson, {Richard F W} and Rees, {Nicholas H} and William Clegg and Heath, {Sarah L}",

note = "CAPLUS AN 1997:707270(Journal)",

year = "1997",

doi = "10.1039/a704534d",

language = "English",

pages = "1855--1856",

journal = "Chem. Commun. (Cambridge)",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "19",

}

TY - JOUR

T1 - Reaction of thiophenol with glucal epoxides: X-ray structure of 3,4,6-tri-O-tert-butyldimethylsilyl-1-S-phenyl-1-thio-α-D-glucopyranoside

AU - Walford, Caroline

AU - Jackson, Richard F W

AU - Rees, Nicholas H

AU - Clegg, William

AU - Heath, Sarah L

N1 - CAPLUS AN 1997:707270(Journal)

PY - 1997

Y1 - 1997

N2 - The reaction of the tert-butyldimethylsilyl protected glucal epoxide with thiophenol under a variety of conditions gives three distinct adducts, including the α-phenylthioglycoside, which exists both in soln. and in the solid state in a 1C4 conformation in which the C-2, C-3, C-4 and C-5 substituents are all axial. [on SciFinder(R)]

AB - The reaction of the tert-butyldimethylsilyl protected glucal epoxide with thiophenol under a variety of conditions gives three distinct adducts, including the α-phenylthioglycoside, which exists both in soln. and in the solid state in a 1C4 conformation in which the C-2, C-3, C-4 and C-5 substituents are all axial. [on SciFinder(R)]

KW - thiophenol reaction glucal epoxide

KW - phenylthioglucopyranoside prepn conformation crystal structure

U2 - 10.1039/a704534d

DO - 10.1039/a704534d

M3 - Article

SN - 1359-7345

SP - 1855

EP - 1856

JO - Chem. Commun. (Cambridge)

JF - Chem. Commun. (Cambridge)

IS - 19

ER -

Reaction of thiophenol with glucal epoxides: X-ray structure of 3,4,6-tri-O-tert-butyldimethylsilyl-1-S-phenyl-1-thio-α-D-glucopyranoside

Abstract

Keywords

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