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Direct Sialic Acid 4-OAc Substitution by Nitrogen, Sulfur and Carbon Nucleophiles with Retention of Stereochemistry

Bozzola, Tiago LU ; Nilsson, Ulf J. LU and Ellervik, Ulf LU orcid (2022) In RSC Advances 12(19). p.11992-11995
Abstract
A direct one-step nucleophilic substitution of the 4-OAc of acetyl protected Neu5Ac is presented. Previously published methods for direct substitution of the 4-OAc are limited to cyclic secondary amines. Here we present conditions that allow for a much wider range of nitrogen nucleophiles as well as thiols and cyanide, to be used. The present investigation significantly broadens the scope of 4-aminations and allows for the introduction of a wide variety of different nucleophiles.
Please use this url to cite or link to this publication:
author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
RSC Advances
volume
12
issue
19
pages
4 pages
publisher
Royal Society of Chemistry
external identifiers
  • pmid:35481106
  • pmid:35481106
ISSN
2046-2069
DOI
10.1039/D2RA01576E
project
Design and synthesis of sialic acid derivatives to block bacterial sialic acid uptake
language
English
LU publication?
yes
id
bac71b95-aabb-42c1-b45d-a9840f3ca128
date added to LUP
2022-05-10 13:41:01
date last changed
2025-04-04 14:36:34
@article{bac71b95-aabb-42c1-b45d-a9840f3ca128,
  abstract     = {{A direct one-step nucleophilic substitution of the 4-OAc of acetyl protected Neu5Ac is presented. Previously published methods for direct substitution of the 4-OAc are limited to cyclic secondary amines. Here we present conditions that allow for a much wider range of nitrogen nucleophiles as well as thiols and cyanide, to be used. The present investigation significantly broadens the scope of 4-aminations and allows for the introduction of a wide variety of different nucleophiles.}},
  author       = {{Bozzola, Tiago and Nilsson, Ulf J. and Ellervik, Ulf}},
  issn         = {{2046-2069}},
  language     = {{eng}},
  number       = {{19}},
  pages        = {{11992--11995}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{RSC Advances}},
  title        = {{Direct Sialic Acid 4-OAc Substitution by Nitrogen, Sulfur and Carbon Nucleophiles with Retention of Stereochemistry}},
  url          = {{http://dx.doi.org/10.1039/D2RA01576E}},
  doi          = {{10.1039/D2RA01576E}},
  volume       = {{12}},
  year         = {{2022}},
}