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METHYL 2-AZIDO-3-O-BENZYL-2-DEOXY-ALPHA-D-MANNOFURANOSIDE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF POLYHYDROXYLATED PIPERIDINES AND PYRROLIDINES - SYNTHESIS OF 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL [2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE]

Abstract:
The synthesis of methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside (1) from D-glucose is reported; the conversions of (1) into derivatives of methyl 3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside (as precursors for the synthesis of polyhydroxylated piperidines) and into the hydroxylated pyrrrolidine, 2,5-dideoxy-2,5-imino-D-mannitol [2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine] are described. © 1987.
Publication status:
Published

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Journal:
TETRAHEDRON
Volume:
43
Issue:
5
Pages:
971-978
Publication date:
1987
DOI:
ISSN:
0040-4020
URN:
uuid:07300ce1-98a5-43a9-89ee-58945dcce22b
Source identifiers:
42756
Local pid:
pubs:42756
Language:
English

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