Comparison of the two anomers of methyl 2-(N-benzylamino)-2, 3-dideoxy-4,6-O-phenylmethylene-3-C-phenylsulfonyl-D-glucopyranoside
The title compounds, the alpha and beta anomers of methyl 2-(N-benzylamino)-2,3-dideoxy-4, 6-O-phenylmethylene-3-C-phenylsulfonyl-D-glucopyranoside, C(27)H(29)NO(6)S, belong to the class of deoxyamino-sugars prepared by the addition of amines at C2. The endocyclic bond lengths of the pyranose ring in the alpha anomer are shorter than the corresponding bonds in the beta anomer. The pyranose ring is in the chair form in the former, while it is in the boat form in the latter. These observed differences could be attributed to the C2 substitution of a bulky group. The phenylsulfonyl and benzylamino groups are in equatorial positions in the alpha anomer, while the benzylamino group is axial in the beta anomer.
Suresh
CG
Division of Biochemical Sciences, National Chemical Laboratory, Pune 411 008, India. suresh@ems.ncl.res.in.
Ravindran
B
Rao
KN
Pathak
T