Preparation of 2-deoxy-2-C-p-tolylsulfonyl-beta-D-glucopyranosyl p-tolylsulfones having non-chair conformation and their elimination reactions.
When the title sulfones, which have non-chair conformations, were stirred with silica gel, elimination of sulfinic acid occurred to give a 1-enitol derivative, if the hydroxyl group at C-6 was protected, whereas such an elimination did not proceed if the hydroxy group was free.
Sakakibara
Tohru
T
Graduate School of Integrated Science, Yokohama City University, 22-2, Seto, Kanazawa-ku, Yokohama 236-0027, Japan. baratoru@yokohama-cu.ac.jp
Suganuma
Tomomi
T
Kajihara
Yasuhiro
Y
D002240:Carbohydrate Sequence; D005947:Glucose / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification; D014105:Tosyl Compounds / Q000737:chemistry*
D013450:Sulfones; D014105:Tosyl Compounds; D005947:Glucose