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- W1970783655 abstract "On the Activation of Partially Silylated Carbohydrates Using Triphenylphosphane/Diethylazodicarboxylate Reaction of methyl α-D-glucopyranoside (1) with two equivalents of t-butyldimethylchlorosilane yields methyl 2,6-bis[O-(t-butyldimethylsilyl)]-α-D-glucopyranoside (1a) and methyl 3,6-bis[O(t-butyldimethylsilyl)]-α-D-glucopyranoside (1b) in a ratio of 4:1. The anomeric β-pyranoside 2 affords methyl 2,6-bis[O(t-butyldimethylsilyl)]-β-D-glucopyranoside (2a) and methyl 3,6-bis[O(t-butyldimethylsilyl)]-β-D-glucopyranoside (2b) in nearly equal amounts. 2b is isomerized to methyl 4,6-bis[O(t-butyldimethylsilyl)]-β;-D-glucopyranoside (2c) (83%) and 2a (10%) with triphenylphosphane/diethylazodicarboxylate. Structures were assigned by NMR.-analysis and CD.-analysis of the corresponding benzoates 1c, 1d and 2d and of the acetates 2e and 2f. 1a is transformed into methyl 4-azido-2, 6-bis[O(t-butyldimethylsilyl)]-4-deoxy-α-D-galactopyranoside (3) with triphenylphosphane/diethylazodicarboxylate/HN3. 2a and 2c yield the 3-azido-allosides 5 and 7 respectively under similar conditions. The activation by triphenylphosphane/diethylazodicarboxylate is high enough to introduce also p-nitrobenzoate groups with inversion of configuration at the reaction center. By this way 1a and 2a give methyl 2, 6-bis[O(t-butyldimethylsilyl)]-4-O-p-nitrobenzoyl-α-D-galactopyranoside (4) and methyl 2, 6-bis[O-(t-butyldimethylsilyl)]-3-O−ptrobenzoyl-β-D-allopyranoside (6) respectively. For elucidation of structures the acetate derivatives 3a-7a were prepared." @default.
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- W1970783655 date "1978-07-12" @default.
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- W1970783655 title "Zur Aktivierung partiell silylierter Kohlenhydrate mittels Triphenylphosphan/Azodicarbonsäureester" @default.
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- W1970783655 doi "https://doi.org/10.1002/hlca.19780610528" @default.
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