A study of the donor properties of sialyl phosphites having an auxiliary 3-(S)-phenylseleno group
(2001) In Carbohydrate Research 331(3). p.255-263- Abstract
- Two phosphite sialyl donors, each having an auxiliary 3-(S)-phenylseleno group, were prepared and evaluated. The phenylseleno group was introduced via a new mode of generating phenylselenenic acid (‘PhSeOH’). Although the sialyl donors provided fair yields (32–76%) of the desired sialosides in glycosylations of the reactive acceptor 1,2;3,4-di-O-isopropylidene-α-d-galactopyranose, no sialylated products could be obtained with less reactive acceptors. The presence of a 5-N-acetylacetamido group on the phosphite sialyl donor did not appear to improve its sialylating capability. The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors α-nitrilium ion formation, seem to explain the... (More)
- Two phosphite sialyl donors, each having an auxiliary 3-(S)-phenylseleno group, were prepared and evaluated. The phenylseleno group was introduced via a new mode of generating phenylselenenic acid (‘PhSeOH’). Although the sialyl donors provided fair yields (32–76%) of the desired sialosides in glycosylations of the reactive acceptor 1,2;3,4-di-O-isopropylidene-α-d-galactopyranose, no sialylated products could be obtained with less reactive acceptors. The presence of a 5-N-acetylacetamido group on the phosphite sialyl donor did not appear to improve its sialylating capability. The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors α-nitrilium ion formation, seem to explain the unsuccessful sialylations of the less reactive acceptors. (Less)
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https://lup.lub.lu.se/record/3a1227ea-c493-459e-a0bd-d48b75de7032
- author
- Ercegovic, Teddy LU ; Nilsson, Ulf J. LU and Magnusson, Göran LU
- organization
- publishing date
- 2001-04-12
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Auxiliary phenylseleno group, Long-range coupling, Phenylselenenic acid, Sialic acid phosphites
- in
- Carbohydrate Research
- volume
- 331
- issue
- 3
- pages
- 9 pages
- publisher
- Elsevier
- external identifiers
-
- scopus:0035848858
- pmid:11383895
- ISSN
- 0008-6215
- DOI
- 10.1016/S0008-6215(01)00029-5
- language
- English
- LU publication?
- yes
- id
- 3a1227ea-c493-459e-a0bd-d48b75de7032
- date added to LUP
- 2023-02-07 08:52:51
- date last changed
- 2024-01-03 22:02:26
@article{3a1227ea-c493-459e-a0bd-d48b75de7032,
abstract = {{Two phosphite sialyl donors, each having an auxiliary 3-(<em>S</em>)-phenylseleno group, were prepared and evaluated. The phenylseleno group was introduced via a new mode of generating phenylselenenic acid (‘PhSeOH’). Although the sialyl donors provided fair yields (32–76%) of the desired sialosides in glycosylations of the reactive acceptor 1,2;3,4-di-<em>O</em>-isopropylidene-α-d-galactopyranose, no sialylated products could be obtained with less reactive acceptors. The presence of a 5-<em>N</em>-acetylacetamido group on the phosphite sialyl donor did not appear to improve its sialylating capability. The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors α-nitrilium ion formation, seem to explain the unsuccessful sialylations of the less reactive acceptors.}},
author = {{Ercegovic, Teddy and Nilsson, Ulf J. and Magnusson, Göran}},
issn = {{0008-6215}},
keywords = {{Auxiliary phenylseleno group; Long-range coupling; Phenylselenenic acid; Sialic acid phosphites}},
language = {{eng}},
month = {{04}},
number = {{3}},
pages = {{255--263}},
publisher = {{Elsevier}},
series = {{Carbohydrate Research}},
title = {{A study of the donor properties of sialyl phosphites having an auxiliary 3-(<i>S</i>)-phenylseleno group}},
url = {{http://dx.doi.org/10.1016/S0008-6215(01)00029-5}},
doi = {{10.1016/S0008-6215(01)00029-5}},
volume = {{331}},
year = {{2001}},
}