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Synthesis and hydroboration of a 3-C-methylene derivative of 2-amino-2-deoxy-D-glucose by Johannes H. Jordaan; Sally Smedley is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Opening of the epoxide ring of methyl 3,3'-anhydro-2-benzamido-4,6-Obenzylidene-2-deoxy-3-C-(hydroxymethyl)-a-o-allopyranoside (1) with sodium iodide, in the presence of acetic anhydride and p-toluenesulfonic acid, gave methyl 3-0acetyl-2-benzamido-4,6-O-benzylidene-2-deoxy-3-C-(iodomethyl)-or-~-allopyranoside (2). Reduction of 2 with powdered zinc in buffered N,N-dimethylformamide gave methyl 2-benzamido-4,6-0-benzylidene-2,3-dideoxy-3-C-methylene-~-D-ro-hexopyranoside (3) in 92% yield. Treatment of 1 with zinc in acetic acid containing sodium iodide afforded 3 directly in 90% yield. Hydroboration-oxidation of 3 gave a mixture of methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-3-C-methyl-a-D-glucopyranoside (6), and the corresponding 3-deoxy-3-C-(hydroxymethyl) derivatives (4). Chromatographic separation of the isomers afforded one of the 3-deoxy-3-C-(hydroxymethyl) 3-epimers as a pure oil, and 6 as an impure oil. Acetylation of the former with acetic anhydride in pyridine gave the 3-deoxy-3-C-(acetoxymethyl) derivative (S), and acetylation of 6 with acetic anhydride containing p-toluenesulfonic acid gave crystalline methyl 3 -U-acetyl-2-benzamido -4,6 -O-benzylidene -2-deoxy-3 -C-me

Who reads Synthesis and hydroboration of a 3-C-methylene derivative of 2-amino-2-deoxy-D-glucose?

Author

Johannes H. Jordaan; Sally Smedley

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1971

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)