PRISMΔDB

Analyze how specific documents activate the features of the SAE. Select a dataset, a run and a document to begin.

Active Features

1518

0.0
Details List
#2637 Feature 2637
3.1
#185 Feature 185
3.1
#2551 Feature 2551
2.8
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2.8
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2.6
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2.4
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2.4
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2.4
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2.3
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2.3
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2.3
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2.1
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2.1
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2.1
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2.1
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2.1
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2.0
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2.0
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2.0
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1.9
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1.9
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1.9
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1.8
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1.8
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1.8
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1.8
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1.8
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1.7
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1.7
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1.7
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1.7
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1.7
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1.7
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1.7
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1.7
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1.7
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.6
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1.5
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1.5
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1.5
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1.5
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1.5
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1.5
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1.5
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1.5
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1.5
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.4
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.3
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.2
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.1
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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1.0
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0.9
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0.9
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0.9
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0.9
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0.9
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0.9
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0.9
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0.9
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0.9
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0.9
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Document Content

Two syntheses of 3-amino-3-deoxy-alpha-D-altropyranosyl 3-amino-3-deoxy-alpha-D-altropyranoside, a new analog of alpha,alpha-trehalose, involving reduction of a diazide and reductive amination of a diketone.
A new diamino sugar, 3-amino-3-deoxy-alpha-D-altropyranosyl 3-amino-3-deoxy-alpha-D-altropyranoside (5) was synthesized by two routes starting from alpha,alpha-trehalose. The first route involved reduction and deprotection of a previously described, benzylidenated diazido analog. The second approach proceeded from the known 2,2'-di-O-benzyl-4,6;4',6'-bis-O-benzylidene derivative of alpha-D-altropyranosyl alpha-D-altropyranoside, to the corresponding 3,3'-diketone, which was subjected to reductive amination with sodium cyanoborohydride and ammonium acetate. The major product, separated in 39% yield from by-products after N-acetylation, was deprotected to give 5. Four by-products were isolated in low yields and determined to be monoaminated analogs which comprise two epimeric, 3'-hydroxy structures and two 3'-epimeric, 3'-cyano-3'-hydroxy structures in their non-aminated residues. A number of observations concerning the 13C- and 1H-n.m.r. spectra of the products are discussed, especially with regard to chemical-shift dependencies for certain ring and substituent protons, and attention is drawn to some inter-residue shielding phenomena.