An efficient synthesis of d-mannoheptulose via oxidation of an olefinated sugar with potassium permanganate in aqueous acetone.
An efficient three-step synthesis of d-mannoheptulose was successfully accomplished from 2,3,4,5,6-penta-O-benzyl-d-mannose. First, an olefinated sugar was prepared from 2,3,4,5,6-penta-O-benzyl-d-mannose via a Wittig reaction. Second, the key step, a 2-hydroxyoxirane product was unexpectedly obtained by oxidation of the olefinated sugar with potassium permanganate in aqueous acetone. Finally d-mannoheptulose was synthesized through debenzylation and hydrolysis in an overall yield of 39%.
Cheng
Jie
J
Nanjing University of Science & Technology, China.
Fang
Zhijie
Z
Li
Song
S
Zheng
Baohui
B
Jiang
Yuhua
Y
D000096:Acetone / Q000737:chemistry*; D008356:Mannoheptulose / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011196:Potassium Permanganate / Q000737:chemistry*
D011196:Potassium Permanganate; D000096:Acetone; D008356:Mannoheptulose