Conformational features of rhamnopyranose derivatives. The molecular structure of methyl 2,3,4-tri- O-acetyl-α- l-rhamnopyranoside

Abstract

Methyl 2,3,4-tri- O-acetyl-α- l-rhamnopyranoside, C 13H 20O 8, M r=304.3, is monoclinic, space group C 2, with a=23.619(1), b=8.2168(5), c=19.093(1) , β=118.72(1)°, V=3249.6(8) 3, D c=1.244 g cm −3, μ (MoK α )=0.97 cm −1 and Z=8. The structure was refined to R=0.044 and R w=0.039 for 1969 observed reflections. There are two independent molecules in the asymmetric unit. The bond lengths and bond angles of the pyranose rings of the two are in good agreement within the limits of error. The molecules have similar conformation except for the orientation of one of the acetoxy groups. Each molecule is a normal 1 C 4 chair with Cremer-Pople puckering parameters Q=0.557(6) , θ=174.6(2)° and ψ=144.6(9)° for molecule A and 0.564(4) , 177.9(1)° and 30.8(8)° for molecule B, respectively. The acetyl groups have the planar, ( S)-cis conformation most commonly observed. They are oriented with the acetyl planes within ±35° of the C-H bond at the ring carbon atom to which they are attached.