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)
(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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https://lup.lub.lu.se/record/14c84cbd-c87d-4779-8041-f44e9187a9dd
- author
- Kihlberg, Jan ; Frejd, Torbjörn LU ; Jansson, Karl ; Sundin, Anders LU and Magnusson, Göran LU
- organization
- publishing date
- 1988-06
- 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}}, }