Crystal structures of two new anomeric 2,3-unsaturated C-glycopyranosides

Jan C.A. Boeyens; S. Don Travlos; Gerhard J. Engelbrecht; Cedric W. Holzapfel; Gert J. Kruger

Crystal structures of two new anomeric 2,3-unsaturated C-glycopyranosides

Jan C.A. Boeyens, S. Don Travlos, Gerhard J. Engelbrecht, Cedric W. Holzapfel, Gert J. Kruger

Chemical Sciences

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

Abstract

The crystal structures of isopropylidene [4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranosyl]- methylmalonate 1 and its β-anomer 2 have been determined by single-crystal X-ray diffraction. Both compounds crystallize with space group P2₁ and cell constants of 1: a, b, c = 10.635 (1), 8.102 (2), 11.212 (1)° β = 107.20 (1)° and 2: a, b, c = 9.995 (1), 10.230 (1), 10.105 (1) Å; β = 115.71 (1)°. The two compounds differ in stereochemistry only at the 1-position which confirms previous conclusions based on nmr spectroscopy. The cyclic fragments in the structures all have related conformations, close to envelope forms. The results confirm that Pd-catalyzed allylic substi-tution proceeds largely with retention of configuration.

Original language	English
Pages (from-to)	48-51
Number of pages	4
Journal	South African Journal of Chemistry
Volume	50
Issue number	1
Publication status	Published - Mar 1997

ASJC Scopus subject areas

General Chemistry

Cite this

@article{b90e7b68ceaf4e5bb6a109ae08c4d693,

title = "Crystal structures of two new anomeric 2,3-unsaturated C-glycopyranosides",

abstract = "The crystal structures of isopropylidene [4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranosyl]- methylmalonate 1 and its β-anomer 2 have been determined by single-crystal X-ray diffraction. Both compounds crystallize with space group P21 and cell constants of 1: a, b, c = 10.635 (1), 8.102 (2), 11.212 (1)° β = 107.20 (1)° and 2: a, b, c = 9.995 (1), 10.230 (1), 10.105 (1) {\AA}; β = 115.71 (1)°. The two compounds differ in stereochemistry only at the 1-position which confirms previous conclusions based on nmr spectroscopy. The cyclic fragments in the structures all have related conformations, close to envelope forms. The results confirm that Pd-catalyzed allylic substi-tution proceeds largely with retention of configuration.",

author = "Boeyens, \{Jan C.A.\} and Travlos, \{S. Don\} and Engelbrecht, \{Gerhard J.\} and Holzapfel, \{Cedric W.\} and Kruger, \{Gert J.\}",

year = "1997",

month = mar,

language = "English",

volume = "50",

pages = "48--51",

journal = "South African Journal of Chemistry",

issn = "0379-4350",

publisher = "Bureau for Scientific Publications",

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TY - JOUR

T1 - Crystal structures of two new anomeric 2,3-unsaturated C-glycopyranosides

AU - Boeyens, Jan C.A.

AU - Travlos, S. Don

AU - Engelbrecht, Gerhard J.

AU - Holzapfel, Cedric W.

AU - Kruger, Gert J.

PY - 1997/3

Y1 - 1997/3

N2 - The crystal structures of isopropylidene [4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranosyl]- methylmalonate 1 and its β-anomer 2 have been determined by single-crystal X-ray diffraction. Both compounds crystallize with space group P21 and cell constants of 1: a, b, c = 10.635 (1), 8.102 (2), 11.212 (1)° β = 107.20 (1)° and 2: a, b, c = 9.995 (1), 10.230 (1), 10.105 (1) Å; β = 115.71 (1)°. The two compounds differ in stereochemistry only at the 1-position which confirms previous conclusions based on nmr spectroscopy. The cyclic fragments in the structures all have related conformations, close to envelope forms. The results confirm that Pd-catalyzed allylic substi-tution proceeds largely with retention of configuration.

AB - The crystal structures of isopropylidene [4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranosyl]- methylmalonate 1 and its β-anomer 2 have been determined by single-crystal X-ray diffraction. Both compounds crystallize with space group P21 and cell constants of 1: a, b, c = 10.635 (1), 8.102 (2), 11.212 (1)° β = 107.20 (1)° and 2: a, b, c = 9.995 (1), 10.230 (1), 10.105 (1) Å; β = 115.71 (1)°. The two compounds differ in stereochemistry only at the 1-position which confirms previous conclusions based on nmr spectroscopy. The cyclic fragments in the structures all have related conformations, close to envelope forms. The results confirm that Pd-catalyzed allylic substi-tution proceeds largely with retention of configuration.

UR - https://www.scopus.com/pages/publications/0040564583

M3 - Article

AN - SCOPUS:0040564583

SN - 0379-4350

VL - 50

SP - 48

EP - 51

JO - South African Journal of Chemistry

JF - South African Journal of Chemistry

IS - 1

ER -

Crystal structures of two new anomeric 2,3-unsaturated C-glycopyranosides

Abstract

ASJC Scopus subject areas

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