The p-methoxybenzyl ether as an in situ-removable carbohydrate-protecting group : A simple one-pot synthesis of the globotetraose tetrasaccharide
(2001) In Journal of the Chemical Society - Perkin Transactions 1 p.886-890- Abstract
- A one-pot synthesis of the globotetraose tetrasaccharide is reported. The synthetic method relies on the use of a p-methoxybenzyl ether as an in situ-removable protecting group. N-Iodosuccinimide/trifluoromethanesulfonic acid-promoted glycosylation of 2-bromoethyl-2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside 5 at −45 °C with phenyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 6 gives an intermediate trisaccharide from which the p-methoxybenzyl
ether is removed by allowing the reaction temperature to rise to 0 °C
for 40 min. Again lowering the... (More) - A one-pot synthesis of the globotetraose tetrasaccharide is reported. The synthetic method relies on the use of a p-methoxybenzyl ether as an in situ-removable protecting group. N-Iodosuccinimide/trifluoromethanesulfonic acid-promoted glycosylation of 2-bromoethyl-2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside 5 at −45 °C with phenyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 6 gives an intermediate trisaccharide from which the p-methoxybenzyl
ether is removed by allowing the reaction temperature to rise to 0 °C
for 40 min. Again lowering the temperature to −45 °C, followed by
addition of methyl 3,4,6-tri-O-acetyl-2-trichloroethoxycarbonylamino-2-deoxy-1-thio-β-D-galactopyranoside 8, affords the globotetraose tetrasaccharide 11 in one-pot in an excellent yield of 76%. (Less)
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https://lup.lub.lu.se/record/14839feb-67df-47a0-8ed5-d9819d91ed3d
- author
- Bhattacharyya, Sumita ; Magnusson, Bengt G. ; Wellmar, Ulf and Nilsson, Ulf J. LU
- organization
- publishing date
- 2001
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of the Chemical Society - Perkin Transactions 1
- issue
- 8
- pages
- 5 pages
- publisher
- Royal Society of Chemistry
- external identifiers
-
- scopus:0034991920
- ISSN
- 1472-7781
- DOI
- 10.1039/b009448j
- language
- English
- LU publication?
- yes
- id
- 14839feb-67df-47a0-8ed5-d9819d91ed3d
- date added to LUP
- 2023-02-07 08:55:00
- date last changed
- 2023-04-03 16:02:51
@article{14839feb-67df-47a0-8ed5-d9819d91ed3d,
abstract = {{A one-pot synthesis of the globotetraose tetrasaccharide is reported. The synthetic method relies on the use of a <em>p</em>-methoxybenzyl ether as an <em>in situ</em>-removable protecting group. <em>N</em>-Iodosuccinimide/trifluoromethanesulfonic acid-promoted glycosylation of 2-bromoethyl-2,3,6-tri-<em>O</em>-benzoyl-4-<em>O</em>-(2,3,6-tri-<em>O</em>-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside <strong>5</strong> at −45 °C with phenyl 2,4,6-tri-<em>O</em>-benzyl-3-<em>O</em>-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside <strong>6</strong> gives an intermediate trisaccharide from which the <em>p</em>-methoxybenzyl<br>
ether is removed by allowing the reaction temperature to rise to 0 °C <br>
for 40 min. Again lowering the temperature to −45 °C, followed by <br>
addition of methyl 3,4,6-tri-<em>O</em>-acetyl-2-trichloroethoxycarbonylamino-2-deoxy-1-thio-β-D-galactopyranoside <strong>8</strong>, affords the globotetraose tetrasaccharide <strong>11</strong> in one-pot in an excellent yield of 76%.}},
author = {{Bhattacharyya, Sumita and Magnusson, Bengt G. and Wellmar, Ulf and Nilsson, Ulf J.}},
issn = {{1472-7781}},
language = {{eng}},
number = {{8}},
pages = {{886--890}},
publisher = {{Royal Society of Chemistry}},
series = {{Journal of the Chemical Society - Perkin Transactions 1}},
title = {{The <i>p</i>-methoxybenzyl ether as an <i>in situ</i>-removable carbohydrate-protecting group : A simple one-pot synthesis of the globotetraose tetrasaccharide}},
url = {{http://dx.doi.org/10.1039/b009448j}},
doi = {{10.1039/b009448j}},
year = {{2001}},
}