Photochemically Based Synthesis of Deoxy Sugars. Synthesis of 2-Deoxy- D - Arabino -Hexopyranose (2-Deoxy- D -Glucose) and Several of Its Derivatives from 3,4,6-Tri- O -Acetyl- D -Glucal

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Abstract
The photolysis of methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-glucopyranoside (2) in 2-propanol results in replacement of the bromine with a hydrogen to give methyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranoside (4) in 91% yield. Similar reactions take place for methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside (3) and a mixture of the a and β anomers of 1,3,4,6-tetra-O-acetyl-2-bromo-2-deoxy-D-glucopyranose (7) and 1,3,4,6-tetra-O-acetyl-2-bromo-2-deoxy-D-mannopyranose (8). Since compounds 2, 3, 7, and 8 each were synthesized from 3,4,6-tri-O-acetyl-D-glucal (1), photochemical reaction appears to be a useful process in 2-deoxy sugar synthesis from glycals.