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Synthetic receptor analogues: preparation and calculated conformations of the 2-deoxy, 6-O-methyl, 6-deoxy, and 6-deoxy-6-fluoro derivatives of methyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside (methyl β-D-galabioside)

Kihlberg, Jan ; Frejd, Torbjörn LU ; Jansson, Karl ; Sundin, Anders LU and Magnusson, Göran LU (1988) In Carbohydrate Research 176(2). p.271-286
Abstract
The 2-deoxy (7), 6-O-methyl (15), 6-deoxy (22), and 6-deoxy-6-fluoro (31) derivatives of methyl β-d-galabioside (1) have been synthesised. Thus, 7 was prepared by xanthate reduction using tributyltin hydride, whereas 22 was obtained by catalytic hydrogenation of a 6-deoxy-6-iodogalabioside. Regioselective mono-fluorination of methyl 2,3-di-O-benzoyl-β-d-galactopyranoside with Et2NSF3 and subsequent α-d-galactosylation provided 31. Molecular mechanics calculations yielded similar conformations for 1, 7, 15, 22, and 31 with differes in... (More)
The 2-deoxy (7), 6-O-methyl (15), 6-deoxy (22), and 6-deoxy-6-fluoro (31) derivatives of methyl β-d-galabioside (1) have been synthesised. Thus, 7 was prepared by xanthate reduction using tributyltin hydride, whereas 22 was obtained by catalytic hydrogenation of a 6-deoxy-6-iodogalabioside. Regioselective mono-fluorination of methyl 2,3-di-O-benzoyl-β-d-galactopyranoside with Et2NSF3 and subsequent α-d-galactosylation provided 31. Molecular mechanics calculations yielded similar conformations for 1, 7, 15, 22, and 31 with differes in φH and ψH of 5°. No indications of intramolecular hydrogen bonds, as displayed by 1 in the crystal, were found for 7, 15, 22, or 31. (Less)
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Carbohydrate Research
volume
176
issue
2
pages
16 pages
publisher
Elsevier
external identifiers
  • scopus:0024287802
ISSN
1873-426X
DOI
10.1016/0008-6215(88)80138-1
language
English
LU publication?
yes
id
14c84cbd-c87d-4779-8041-f44e9187a9dd
date added to LUP
2022-05-16 17:40:41
date last changed
2022-05-19 13:49:59
@article{14c84cbd-c87d-4779-8041-f44e9187a9dd,
  abstract     = {{The 2-deoxy (<strong>7</strong>), 6-<em>O</em>-methyl (<strong>15</strong>), 6-deoxy (<strong>22</strong>), and 6-deoxy-6-fluoro (<strong>31</strong>) derivatives of methyl β-d-galabioside (<strong>1</strong>) have been synthesised. Thus, <strong>7</strong> was prepared by xanthate reduction using tributyltin hydride, whereas <strong>22</strong> was obtained by catalytic hydrogenation of a 6-deoxy-6-iodogalabioside. Regioselective mono-fluorination of methyl 2,3-di-<em>O</em>-benzoyl-β-d-galactopyranoside with Et<sub>2</sub>NSF<sub>3</sub> and subsequent α-d-galactosylation provided <strong>31</strong>. Molecular mechanics calculations yielded similar conformations for <strong>1, 7, 15, 22</strong>, and <strong>31</strong> with differes in φ<sub>H</sub> and ψ<sub>H</sub> of 5°. No indications of intramolecular hydrogen bonds, as displayed by <strong>1</strong> in the crystal, were found for <strong>7, 15, 22,</strong> or <strong>31</strong>.}},
  author       = {{Kihlberg, Jan and Frejd, Torbjörn and Jansson, Karl and Sundin, Anders and Magnusson, Göran}},
  issn         = {{1873-426X}},
  language     = {{eng}},
  number       = {{2}},
  pages        = {{271--286}},
  publisher    = {{Elsevier}},
  series       = {{Carbohydrate Research}},
  title        = {{Synthetic receptor analogues: preparation and calculated conformations of the 2-deoxy, 6-<i>O</i>-methyl, 6-deoxy, and 6-deoxy-6-fluoro derivatives of methyl 4-<i>O</i>-α-D-galactopyranosyl-β-D-galactopyranoside (methyl β-D-galabioside)}},
  url          = {{http://dx.doi.org/10.1016/0008-6215(88)80138-1}},
  doi          = {{10.1016/0008-6215(88)80138-1}},
  volume       = {{176}},
  year         = {{1988}},
}