Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis

Daniel L. Jensen; Helle H. Trinderup; Frederik Skovbo; Henrik H. Jensen

doi:10.1039/d2ob00939k

Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis

Daniel L. Jensen, Helle H. Trinderup, Frederik Skovbo, Henrik H. Jensen^*

^*Corresponding author af dette arbejde

Institut for Kemi

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

5 Citationer (Scopus)

Abstract

A new and environmentally friendly protocol for the conversion of sugar per-acetates into thioglycosides under solvent free and catalytic conditions is presented. The procedure involves heating in the presence of InCl₃ and various aryl thiols. For alkyl thioglycoside synthesis, cyclohexane thiol was found to give good results and yield a glycosyl donor with reactivity similar to a thioethyl congener. The established optimum reaction conditions were found to provide the desired thioglycoside products in an easy and highly diastereoselective manner even when conducted on a multigram scale.

Originalsprog	Engelsk
Tidsskrift	Organic and Biomolecular Chemistry
Vol/bind	20
Nummer	24
Sider (fra-til)	4915-4925
Antal sider	11
ISSN	1477-0520
DOI	https://doi.org/10.1039/d2ob00939k
Status	Udgivet - maj 2022

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title = "Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis",

abstract = "A new and environmentally friendly protocol for the conversion of sugar per-acetates into thioglycosides under solvent free and catalytic conditions is presented. The procedure involves heating in the presence of InCl3 and various aryl thiols. For alkyl thioglycoside synthesis, cyclohexane thiol was found to give good results and yield a glycosyl donor with reactivity similar to a thioethyl congener. The established optimum reaction conditions were found to provide the desired thioglycoside products in an easy and highly diastereoselective manner even when conducted on a multigram scale.",

author = "Jensen, {Daniel L.} and Trinderup, {Helle H.} and Frederik Skovbo and Jensen, {Henrik H.}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry",

year = "2022",

month = may,

doi = "10.1039/d2ob00939k",

language = "English",

volume = "20",

pages = "4915--4925",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "24",

}

Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis. / Jensen, Daniel L.; Trinderup, Helle H.; Skovbo, Frederik et al.
I: Organic and Biomolecular Chemistry, Bind 20, Nr. 24, 05.2022, s. 4915-4925.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

TY - JOUR

T1 - Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis

AU - Jensen, Daniel L.

AU - Trinderup, Helle H.

AU - Skovbo, Frederik

AU - Jensen, Henrik H.

PY - 2022/5

Y1 - 2022/5

N2 - A new and environmentally friendly protocol for the conversion of sugar per-acetates into thioglycosides under solvent free and catalytic conditions is presented. The procedure involves heating in the presence of InCl3 and various aryl thiols. For alkyl thioglycoside synthesis, cyclohexane thiol was found to give good results and yield a glycosyl donor with reactivity similar to a thioethyl congener. The established optimum reaction conditions were found to provide the desired thioglycoside products in an easy and highly diastereoselective manner even when conducted on a multigram scale.

AB - A new and environmentally friendly protocol for the conversion of sugar per-acetates into thioglycosides under solvent free and catalytic conditions is presented. The procedure involves heating in the presence of InCl3 and various aryl thiols. For alkyl thioglycoside synthesis, cyclohexane thiol was found to give good results and yield a glycosyl donor with reactivity similar to a thioethyl congener. The established optimum reaction conditions were found to provide the desired thioglycoside products in an easy and highly diastereoselective manner even when conducted on a multigram scale.

UR - http://www.scopus.com/inward/record.url?scp=85131795160&partnerID=8YFLogxK

U2 - 10.1039/d2ob00939k

DO - 10.1039/d2ob00939k

M3 - Journal article

C2 - 35678647

AN - SCOPUS:85131795160

SN - 1477-0520

VL - 20

SP - 4915

EP - 4925

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

Solvent free, catalytic and diastereoselective preparation of aryl and alkyl thioglycosides as key components for oligosaccharide synthesis

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