O-ethyl and o-methyl n-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyl)thiocarbamate

S Zhang; Z Wang; M Li; K Jiao; I A Razak; S Shanmuga Sundara Raj; H K Fun

doi:10.1107/s0108270101000609

O-ethyl and o-methyl n-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyl)thiocarbamate

Acta Crystallogr C. 2001 May;57(Pt 5):566-8. doi: 10.1107/s0108270101000609. Epub 2001 May 15.

Authors

S Zhang¹, Z Wang, M Li, K Jiao, I A Razak, S Shanmuga Sundara Raj, H K Fun

Affiliation

¹ Department of Applied Chemistry, Qingdao Institute of Chemical Technology, Qingdao 266042, People's Republic of China.

PMID: 11353253
DOI: 10.1107/s0108270101000609

Abstract

In both the title structures, O-ethyl N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamate, C(17)H(25)NO(10)S, and O-methyl N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamate, C(16)H(23)NO(10)S, the hexopyranosyl ring adopts the (4)C(1) conformation. All the ring substituents are in equatorial positions. The acetoxymethyl group is in a gauche-gauche conformation. The S atom is in a synperiplanar conformation, while the C-N-C-O linkage is antiperiplanar. N-H.O intermolecular hydrogen bonds link the molecules into infinite chains and these are connected by C-H.O interactions.

MeSH terms

Carbohydrate Conformation
Glucosides / chemistry*
Isomaltose / chemistry
Thiocarbamates / chemistry*

Substances

Glucosides
O-ethyl N-(2,3,4,6-tetra-O-acetylglucopyranosyl)thiocarbamate
O-methyl N-(2,3,4,6-tetra-O-acetylglucopyranosyl)thiocarbamate
Thiocarbamates
Isomaltose