Synthesis of some methylated tetroses and pentoses | Zendy

Guy G.S. Dutton | Zendy; K.B. Gibney | Zendy; P. E. Reid | Zendy

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Synthesis of some methylated tetroses and pentoses

Author(s) -

Guy G.S. Dutton,

K.B. Gibney,

P. E. Reid

Publication year - 1969

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v69-411

Subject(s) - chemistry , periodate , erythritol , stereochemistry , borohydride , xylose , methyl oleate , methyl ketone , mannitol , methyl group , medicinal chemistry , organic chemistry , fermentation , biochemistry , catalysis , alkyl

Oxidation of 2,3-di-O-methyl-D-glucitol (≡ 4,5-di-O-methyl-L-gulitol) and 2,3-di-O-methyl-D-mannitol (≡ 4,5-di-O-methyl-D-mannitol) with an excess of periodate gave 2,3-di-O-methyl-L-threose and 2,3-di-O-methyl-D-erythrose, each characterized as the 2,4-dinitrophenylhydrazone. Borohydride reduction of the sugars gave 2,3-di-O-methyl-L-threitol and 2,3-di-O-methylerythritol characterized as their di-p-nitrobenzoates. Oxidation of the hexitols with 1 mole of periodate gave 3,4-di-O-methyl-L-xylose characterized as methyl 3,4-di-O-methyl-α-L-xylopyranoside and 3,4-di-O-methyl-D-arabinose identified as 3,4-di-O-methyl-D-arabonamide. 2-O-Methyl-D-erythritol (≡ 3-O-methyl-L-erythritol) and 1-O-methyl-D-threitol (≡ 4-O-methyl-D-threitol) were also prepared and characterized as the tri-p-nitrobenzoates.

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