Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-b-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-a-D-mannopyranoside

Krist, P., Kuzma, M., Pelyvás, I. F., Simerská, P. and Křen, V. (2003) Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-b-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-a-D-mannopyranoside. Collection of Czechoslovak Chemical Communications, 68 4: 801-811. doi:10.1135/cccc20030801


Author Krist, P.
Kuzma, M.
Pelyvás, I. F.
Simerská, P.
Křen, V.
Title Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-b-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-a-D-mannopyranoside
Journal name Collection of Czechoslovak Chemical Communications   Check publisher's open access policy
ISSN 0010-0765
Publication date 2003
Sub-type Article (original research)
DOI 10.1135/cccc20030801
Volume 68
Issue 4
Start page 801
End page 811
Total pages 11
Place of publication Prague, Czech Republic
Publisher Akademie Ved Ceske Republiky Ustav Organicke Chemie a Biochemie
Formatted abstract
The title compounds were synthesized by the selective reduction of the azido group in 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (8) and 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside (11), and by subsequent acetylation. Compound 8 was prepared by opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-glucopyranoside (1) with sodium azide, followed by inversion of the configuration at C-3 in the resulting altropyranoside and glycosidation with 4-nitrophenol.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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Created: Tue, 27 Sep 2011, 16:53:38 EST by Dr Pavla Simerska on behalf of School of Chemistry & Molecular Biosciences