Crystal and molecular structures of 2,3,4,6-tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile

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Abstract

2,3,4,6-Tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide (1) and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile (2) crystallise in the orthorhombic system; 1 has space group P212121, with cell dimensions a = 7.256(1), b = 8.957(2), c = 29.450(3) Å, and 2 has space group P212121, with a = 7.035(1), b = 15.080(2), c = 19.635(3) Å. The earlier observation, inferred from n.m.r. data, that the reaction of 1 with silver or mercury(II) acetate in acetic acid-acetic anhydride gave 2 with inversion of configuration at the cyanid-bearing carbon is substantiated. The presence of Br in 1 permitted establishment of the absolute configuration.

Original languageEnglish
Pages (from-to)1-5
Number of pages5
JournalCarbohydrate Research
Volume168
Issue number1
DOIs
Publication statusPublished - Oct 15 1987

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Bearings (structural)
Rubiaceae
Cyanides
Molecular Structure
Mercury
Silver
Acetic Acid
Molecular structure
Acetates
Carbon
Crystal structure
Observation
acetic anhydride

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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title = "Crystal and molecular structures of 2,3,4,6-tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile",
abstract = "2,3,4,6-Tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide (1) and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile (2) crystallise in the orthorhombic system; 1 has space group P212121, with cell dimensions a = 7.256(1), b = 8.957(2), c = 29.450(3) {\AA}, and 2 has space group P212121, with a = 7.035(1), b = 15.080(2), c = 19.635(3) {\AA}. The earlier observation, inferred from n.m.r. data, that the reaction of 1 with silver or mercury(II) acetate in acetic acid-acetic anhydride gave 2 with inversion of configuration at the cyanid-bearing carbon is substantiated. The presence of Br in 1 permitted establishment of the absolute configuration.",
author = "L. P{\'a}rk{\'a}ny{\'i} and A. K{\'a}lm{\'a}n and L. Soms{\'a}k and Istv{\'a}n Farkas",
year = "1987",
month = "10",
day = "15",
doi = "10.1016/0008-6215(87)80001-0",
language = "English",
volume = "168",
pages = "1--5",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "1",

}

TY - JOUR

T1 - Crystal and molecular structures of 2,3,4,6-tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile

AU - Párkányí, L.

AU - Kálmán, A.

AU - Somsák, L.

AU - Farkas, István

PY - 1987/10/15

Y1 - 1987/10/15

N2 - 2,3,4,6-Tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide (1) and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile (2) crystallise in the orthorhombic system; 1 has space group P212121, with cell dimensions a = 7.256(1), b = 8.957(2), c = 29.450(3) Å, and 2 has space group P212121, with a = 7.035(1), b = 15.080(2), c = 19.635(3) Å. The earlier observation, inferred from n.m.r. data, that the reaction of 1 with silver or mercury(II) acetate in acetic acid-acetic anhydride gave 2 with inversion of configuration at the cyanid-bearing carbon is substantiated. The presence of Br in 1 permitted establishment of the absolute configuration.

AB - 2,3,4,6-Tetra-O-acetyl-1-bromo-d-galactopyranosyl cyanide (1) and 2,3,4,5,7-penta-O-acetyl-β-d-galacto-2-heptulopyranosononitrile (2) crystallise in the orthorhombic system; 1 has space group P212121, with cell dimensions a = 7.256(1), b = 8.957(2), c = 29.450(3) Å, and 2 has space group P212121, with a = 7.035(1), b = 15.080(2), c = 19.635(3) Å. The earlier observation, inferred from n.m.r. data, that the reaction of 1 with silver or mercury(II) acetate in acetic acid-acetic anhydride gave 2 with inversion of configuration at the cyanid-bearing carbon is substantiated. The presence of Br in 1 permitted establishment of the absolute configuration.

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