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• W2073431232 abstract "Structural Modification on Partially Silylated Carbohydrates by Means of Triphenylphosphine/Diethyl AzodicarboxylateReaction of methyl 2, 6-bis-O-(t-butyldimethylsilyl)-β-D-glucopyranoside (1a) with triphenylphosphine (TPP)/diethyl azodicarboxylate (DEAD) and Ph3P · HBr or methyl iodide yields methyl 3-bromo-2, 6-bis-O-(t-butyldimethylsilyl)-3-deoxy-β-D-allopyranoside (3a) and the corresponding 3-deoxy-3-iodo-alloside 3c(Scheme 1). By a similar way methyl 2, 6-bis-O-(t-butyldimethylsilyl)-α-D-glucopyranoside (2a) can be converted to the 4-bromo-4-deoxy-galactoside 4a and the 4-deoxy-4-iodo-galactoside 4b. In the absence of an external nucleophile the sugar derivatives 1a and 2a react with TPP/DEAD to form the 3,4-anhydro-α- or -β-D-galactosides 5 and 6a, respectively, while methyl 4, 6-bis-O-(t-butyldimethylsilyl)-β-D-glucopyranoside (1b) yields methyl 2,3-anhydro-4, 6-bis-O-(t-butyldimethylsilyl)-β-D-allopyranoside (7a, s. Scheme 2). Even the monosilylated sugar methyl 6-O-(t-butyldimethylsilyl)-α-D-glucopyranoside (2b) can be transformed to methyl 2,3-anhydro-6-O-(t-butyldimethylsilyl)-β-D-allopyranoside (8; 56%) and 3,4-anhydro-α-D-alloside 9 (23%, s. Scheme 3). Reaction of 1c with TPP/DEAD/HN3 leads to methyl 3-azido-6-O-(t-butyldimethylsilyl)-3-deoxy-β-D-allopyranoside (10). The epoxides 7 and 8 were converted with NaN3/NH4Cl to the 2-azido-2-deoxy-altrosides 11 and 13, respectively, and the 3-azido-3-deoxy-glucosides 12 and 14, respectively (Scheme 4 and 5). Reaction of 7 and 8 with TPP/DEAD/HN3 or p-nitrobenzoic acid afforded methyl 2,3-anhydro-4-azido-6-O-(t-butyldimethylsilyl)-4-deoxy-α- and -β-D-gulopyranoside (15 and 17), respectively, or methyl 2,3-anhydro-6-O-(t-butyldimethylsilyl)-4-O-(p-nitrobenzoyl)-α- and -β-D-gulopyranoside (16 and 18), respectively, without any opening of the oxirane ring (s. Scheme 6). - The 2-acetamido-2-deoxy-glucosides 19a and 20a react with TPP/DEAD alone to form the corresponding methyl 2-acetamido-3,4-anhydro-6-O-(t-butyldimethylsilyl)-2-deoxy-galactopyranosides (21 and 22) in a yield of 80 and 85%, respectively (Scheme 7). With TPP/DEAD/HN320a is transformed to methyl 2-acetamido-3-azido-6-O-(t-butyldimethylsilyl)-2,3-didesoxy-β-D-allopyranoside (25, Scheme 8). By this way methyl 2-acetamido-3,6-bis-O-(t-butyldimethylsilyl)-α-D-glucopyranoside (19b) yields methyl 2-acetamido-4-azido-3,6-bis-O-(t-butyldimethylsilyl)-2,4-dideoxy-α-D-galactopyranoside (23; 16%) and the isomerized product methyl 2-acetamido-4,6-bis-O-(t-butyldimethylsilyl)-2-deoxy-α-D-glucopyranoside (19d; 45%). Under the same conditions the disilylated methyl 2-acetamido-2-deoxy-glucoside 20b leads to methyl 2-acetamido-4-azido-3,6-bis-O-(t-butyldimethylsilyl)-2,4-dideoxy-β-D-galactopyranoside (24). - All Structures were assigned by 1H-NMR. analysis of the corresponding acetates." @default.
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• W2073431232 date "1980-03-05" @default.
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• W2073431232 title "Strukturelle Abwandlungen an partiell silylierten Kohlenhydraten mittels Triphenylphosphin/Azodicarbonsäure-diäthylester. 3. Mitteilung [1]" @default.
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