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Prespacer Glycosides in Glycoconjugate Chemistry. Dibromoisobutyl (DIB) Glycosides for the Synthesis of Neoglycolipids, Neoglycoproteins, Neoglycoparticles, and Soluble Glycosides

Magnusson, Göran LU ; Ahlfors, Stefan ; Dahmén, Jan ; Jansson, Karl ; Nilsson, Ulf LU ; Noori, Ghazi ; Stenvall, Kristina and Tjörnebo, Ann (1990) In Journal of Organic Chemistry 55(12). p.3932-3946
Abstract

3-Bromo-2-(bromomethyl)propyl (dibromoisobutyl or DIB) mono- to tetrasaccharide glycosides were prepared in moderate to high yields by treatment of the corresponding 1-0-acetyl saccharides with 3-bromo-2-(bromo-methyl)propanol (DIBOL) and boron trifluoride etherate. Treatment of the DIB glycosides with alkyl- and ω-methoxycarbonylalkyl thiols gave the corresponding bis-sulfide glycolipids and spacer arm sugars, respectively. Oxidation of the sulfides with m-chloroperbenzoic acid gave the corresponding bis-sulfones. Treatment of the DIB glycosides with tetrabutylammonium fluoride gave the corresponding allylic bromide glycosides, and addition of thiols gave the allylic sulfides. Prolonged fluoride treatment gave the... (More)

3-Bromo-2-(bromomethyl)propyl (dibromoisobutyl or DIB) mono- to tetrasaccharide glycosides were prepared in moderate to high yields by treatment of the corresponding 1-0-acetyl saccharides with 3-bromo-2-(bromo-methyl)propanol (DIBOL) and boron trifluoride etherate. Treatment of the DIB glycosides with alkyl- and ω-methoxycarbonylalkyl thiols gave the corresponding bis-sulfide glycolipids and spacer arm sugars, respectively. Oxidation of the sulfides with m-chloroperbenzoic acid gave the corresponding bis-sulfones. Treatment of the DIB glycosides with tetrabutylammonium fluoride gave the corresponding allylic bromide glycosides, and addition of thiols gave the allylic sulfides. Prolonged fluoride treatment gave the allylic fluorides. Hydrogenation of DIB glycosides under basic conditions gave the corresponding isobutyl glycosides. Spacer arm and allylic bromide glycosides were coupled to bovine serum albumin and derivatized silica gel, thereby providing artificial glycoprothins and glycoparticles.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
55
issue
12
pages
15 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:0025158351
ISSN
0022-3263
DOI
10.1021/jo00299a044
language
English
LU publication?
yes
id
2b72526b-dbee-4a7e-ba5f-195cd61e4076
date added to LUP
2023-02-07 10:05:47
date last changed
2023-02-27 13:07:12
@article{2b72526b-dbee-4a7e-ba5f-195cd61e4076,
  abstract     = {{<p>3-Bromo-2-(bromomethyl)propyl (dibromoisobutyl or DIB) mono- to tetrasaccharide glycosides were prepared in moderate to high yields by treatment of the corresponding 1-<i>0</i>-acetyl saccharides with 3-bromo-2-(bromo-methyl)propanol (DIBOL) and boron trifluoride etherate. Treatment of the DIB glycosides with alkyl- and <i>ω</i>-methoxycarbonylalkyl thiols gave the corresponding bis-sulfide glycolipids and spacer arm sugars, respectively. Oxidation of the sulfides with <i>m</i>-chloroperbenzoic acid gave the corresponding bis-sulfones. Treatment of the DIB glycosides with tetrabutylammonium fluoride gave the corresponding allylic bromide glycosides, and addition of thiols gave the allylic sulfides. Prolonged fluoride treatment gave the allylic fluorides. Hydrogenation of DIB glycosides under basic conditions gave the corresponding isobutyl glycosides. Spacer arm and allylic bromide glycosides were coupled to bovine serum albumin and derivatized silica gel, thereby providing artificial glycoprothins and glycoparticles.</p>}},
  author       = {{Magnusson, Göran and Ahlfors, Stefan and Dahmén, Jan and Jansson, Karl and Nilsson, Ulf and Noori, Ghazi and Stenvall, Kristina and Tjörnebo, Ann}},
  issn         = {{0022-3263}},
  language     = {{eng}},
  number       = {{12}},
  pages        = {{3932--3946}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Organic Chemistry}},
  title        = {{Prespacer Glycosides in Glycoconjugate Chemistry. Dibromoisobutyl (DIB) Glycosides for the Synthesis of Neoglycolipids, Neoglycoproteins, Neoglycoparticles, and Soluble Glycosides}},
  url          = {{http://dx.doi.org/10.1021/jo00299a044}},
  doi          = {{10.1021/jo00299a044}},
  volume       = {{55}},
  year         = {{1990}},
}