(+/-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside → (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Participants

Reaction Steps

The diastereomer mixture (5a) was resolved by means of silica gel column chromatography using ethyl acetate as an eluent. As a result, (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6a) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7a) were obtained in white-solid form and in yields of 1.8 g and 1.7 g, respectively. Further, (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6a) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7a) were each recrystallized from ethyl acetate-hexane. As a result, highly purified (S)-(-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (6a) and (R)-(+)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6tetra-O-acetyl-β-D-glucopyranoside (7a) were obtained in yields of 1.7 g (30%) and 1.6 g (28%), respectively.

Provenance & Evidence