O-ethyl and o-methyl n-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyl)thiocarbamate.
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.
Zhang
S
S
Department of Applied Chemistry, Qingdao Institute of Chemical Technology, Qingdao 266042, People's Republic of China.
Wang
Z
Z
Li
M
M
Jiao
K
K
Razak
I A
IA
Shanmuga Sundara Raj
S
S
Fun
H K
HK
D002236:Carbohydrate Conformation; D005960:Glucosides / Q000737:chemistry*; D007534:Isomaltose / Q000737:chemistry; D013859:Thiocarbamates / Q000737:chemistry*
D005960:Glucosides; C431288:O-ethyl N-(2,3,4,6-tetra-O-acetylglucopyranosyl)thiocarbamate; C431287:O-methyl N-(2,3,4,6-tetra-O-acetylglucopyranosyl)thiocarbamate; D013859:Thiocarbamates; D007534:Isomaltose