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2-(Trimethylsilyl)ethyl Glycosides. Transformation into the Corresponding. 1-O-Acyl Sugars

Ellervik, Ulf LU orcid and Magnusson, Göran LU (1993) In Acta Chemica Scandinavica 47(8). p.826-828
Abstract
(Trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside and (trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,6-tri-O-acetyl-4-O-[2-acetamido-4,6-di-O-ace tyl-2- deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D- galactopyranosyl]-beta-D-galactopyranosyl)-beta-D-glucopyranoside have been transformed in high yield into the corresponding 1-O-beta-acyl saccharides by treatment with various carboxylic anhydrides in the presence of boron trifluoride-diethyl ether in toluene. The carboxylic anhydrides (4-pentenoic, 2-cyclopentenylacetic, 2,4-dimethoxy-benzoic, and 2-methoxybenzoic anhydride) were synthesized from the corresponding carboxylic acids by treatment with N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic... (More)
(Trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside and (trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,6-tri-O-acetyl-4-O-[2-acetamido-4,6-di-O-ace tyl-2- deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D- galactopyranosyl]-beta-D-galactopyranosyl)-beta-D-glucopyranoside have been transformed in high yield into the corresponding 1-O-beta-acyl saccharides by treatment with various carboxylic anhydrides in the presence of boron trifluoride-diethyl ether in toluene. The carboxylic anhydrides (4-pentenoic, 2-cyclopentenylacetic, 2,4-dimethoxy-benzoic, and 2-methoxybenzoic anhydride) were synthesized from the corresponding carboxylic acids by treatment with N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride. (Less)
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author
and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Acta Chemica Scandinavica
volume
47
issue
8
pages
826 - 828
publisher
Munksgaard Forlag
external identifiers
  • scopus:0027652243
ISSN
0904-213X
DOI
10.3891/acta.chem.scand.47-0826
language
English
LU publication?
yes
id
76a1e625-e67d-48e1-8512-365aea43881e
date added to LUP
2023-08-10 15:06:44
date last changed
2024-01-05 04:06:27
@article{76a1e625-e67d-48e1-8512-365aea43881e,
  abstract     = {{(Trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside and (trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,6-tri-O-acetyl-4-O-[2-acetamido-4,6-di-O-ace tyl-2- deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D- galactopyranosyl]-beta-D-galactopyranosyl)-beta-D-glucopyranoside have been transformed in high yield into the corresponding 1-O-beta-acyl saccharides by treatment with various carboxylic anhydrides in the presence of boron trifluoride-diethyl ether in toluene. The carboxylic anhydrides (4-pentenoic, 2-cyclopentenylacetic, 2,4-dimethoxy-benzoic, and 2-methoxybenzoic anhydride) were synthesized from the corresponding carboxylic acids by treatment with N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride.}},
  author       = {{Ellervik, Ulf and Magnusson, Göran}},
  issn         = {{0904-213X}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{826--828}},
  publisher    = {{Munksgaard Forlag}},
  series       = {{Acta Chemica Scandinavica}},
  title        = {{2-(Trimethylsilyl)ethyl Glycosides. Transformation into the Corresponding. 1-O-Acyl Sugars}},
  url          = {{http://dx.doi.org/10.3891/acta.chem.scand.47-0826}},
  doi          = {{10.3891/acta.chem.scand.47-0826}},
  volume       = {{47}},
  year         = {{1993}},
}