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)

Jan Kihlberg; Torbjörn Frejd; Karl Jansson; Anders Sundin; Göran Magnusson

doi:10.1016/0008-6215(88)80138-1

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)

Jan Kihlberg, Torbjörn Frejd, Karl Jansson, Anders Sundin, Göran Magnusson

Centre for Analysis and Synthesis

Lund University

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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 φ_H and ψ_H of 5°. No indications of intramolecular hydrogen bonds, as displayed by 1 in the crystal, were found for 7, 15, 22, or 31.

Original language	English
Pages (from-to)	271-286
Number of pages	16
Journal	Carbohydrate Research
Volume	176
Issue number	2
DOIs	https://doi.org/10.1016/0008-6215(88)80138-1
Publication status	Published - 1988 Jun

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Organic Chemistry

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Kihlberg, J., Frejd, T., Jansson, K., Sundin, A., & Magnusson, G. (1988). 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). Carbohydrate Research, 176(2), 271-286. https://doi.org/10.1016/0008-6215(88)80138-1

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title = "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)",

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 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.",

author = "Jan Kihlberg and Torbj{\"o}rn Frejd and Karl Jansson and Anders Sundin and G{\"o}ran Magnusson",

year = "1988",

month = jun,

doi = "10.1016/0008-6215(88)80138-1",

language = "English",

volume = "176",

pages = "271--286",

journal = "Carbohydrate Research",

issn = "1873-426X",

publisher = "Elsevier",

number = "2",

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Kihlberg, J, Frejd, T, Jansson, K, Sundin, A & Magnusson, G 1988, '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)', Carbohydrate Research, vol. 176, no. 2, pp. 271-286. https://doi.org/10.1016/0008-6215(88)80138-1

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; Jansson, Karl et al.
In: Carbohydrate Research, Vol. 176, No. 2, 06.1988, p. 271-286.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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)

AU - Kihlberg, Jan

AU - Frejd, Torbjörn

AU - Jansson, Karl

AU - Sundin, Anders

AU - Magnusson, Göran

PY - 1988/6

Y1 - 1988/6

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0024287802

U2 - 10.1016/0008-6215(88)80138-1

DO - 10.1016/0008-6215(88)80138-1

M3 - Article

SN - 1873-426X

VL - 176

SP - 271

EP - 286

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 2

ER -

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)

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